5 Probing Tips that Will Deepen ANY Conversation

To probe.

It is what lawyers do. Investigators. Therapists. Or perhaps the frustrated parent who seeks to extract information from a recalcitrant child. Right?

I hear the word “probe,” and I think congressional hearings. Politicians hovering in elevated seats, staring down at a solitary witness with a prosecutorial air. Probing, probing, probing, probing.

A spectacle. Given this context, it’s easy to forget that terrific things can happen in a simple everyday conversation when we probe with a measure of grace. Not the lawyer/prosecutor/interrogator probing. No, probing for greater personal connection.

The important thing is not to stop questioning. Curiosity has its own reason for existence."

Albert Einstein

Lynne Waymon is the former CEO of Contact Counts, a training firm that teaches professionals how to better network, and the co-author of “Strategic Connections: The New Face of Networking in a Collaborative World.” In a survey her firm conducted with over 1000 professionals, Waymon found that only 1 out of 4 professionals saw value in asking probing questions of strangers.

I’m shocked. We’re not talking senate-hearing-probe here. We’re talking probing to elevate everyday relationships.

Everyday probing, Waymon explains, involves taking a risk. I’m demanding more of you when I ask thought-provoking questions. I’m making an assumption that you’re in this conversation to make something of it.

Risky, yes. But every business relationship blossoms when we consciously probe and take a risk. Want to minimize the risk? Here are my Top 5 Conversational Probing Tips. They work in business and in absolutely every aspect of your life.

  1. Always a 2-fer

When you ask someone a question, think Question/Answer/Follow-up Question. The second question confirms that you have heard, that you’re interested, and that you long to know more. It demonstrates curiosity. It’s the relationship builder.

The exception? When the first question creates clear discomfort or disinterest in your conversation, notice the discomfort and move on, unless it is time to have an intentionally disruptive conversation with this individual.

  1. The low-risk probe

Asking for specifics as you probe is simple, surefire, and the least risky way of advancing and deepening any conversation.

Statement:  I had such a great time in New York over the week-end.
Question:  What did you enjoy most during your visit?

Sounds obvious, doesn’t it? But how often have you spoken with someone who immediately starts telling you how SHE always wanted to visit New York or how he had an amazing time on HIS last trip to the Big Apple. Probing opportunity wasted.

You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions." 

Naguib Mahfouz

  1. The high-impact probe

Asking for the WHY drives a conversation to the other person’s deeper purpose and motivation. Your conversation drops to a more intimate, more vulnerable and ultimately more enriching level. It is simply inevitable.

Statement:  I just love spending time in New York.
Question:  Why do you think you enjoy being in New York so much?

  1. The what-did-you-feel probe

Asking to name an emotion may seem a little therapy-ish to you. Overuse it, and folks may indeed tell you to stop “being my shrink.” But our emotions are the hidden level beyond thought where we commit to, or resist, any situation or experience. Naming an emotion will invariably invite powerful personal testimony.

Statement:  I had such a great time in New York.
Question:  So how did it actually feel to be running around in New York?

  1. Know when to un-probe

I hang out with professional coaches. Many of them are masters at asking probing questions. Coaches have also been trained to keep themselves out of the conversation. While that may work in a coaching conversation, it NEVER works in a business conversation. Keep probing and probing, and you become one of those investigator-probing-machines, even when you do it with a smile. Stop it.

Want to deepen a relationship? Probe, probe, and then find a sincere AND substantive link to your own experiences.

It’s so very clear. If you want to succeed in your relationships – any relationships – asking a probing question is a non-negotiable skill. NOT probing isn’t an option.

Tis the holiday season. Chances are, you will engage with more people than usual. Don’t ask the probing questions like a prosecutor, ask them with grace. But ask. Ask them often.

And reap the rewards.

My 3 Favorite Thanksgiving Questions

How far can we push? What can I learn? Not how to make a movie – just about life. Know what I mean?

That’s Martin Scorsese, considered one of the greatest living filmmakers around, as quoted by John Jurgensen in his current essay about Scorsese in the November 2023 issue of The Wall Street Journal Magazine (Jurgensen, WSJ, “Flip the Script.”).

Yes, Martin, know what you mean.

Scorsese is 81 years old. His recent movie, Flowers of the Killer Moon, is a revelation of more brilliance from an astounding filmmaker. “After 60 years as a filmmaker, Martin Scorsese is still growing,” Jurgensen affirms in his piece.


It’s Thanksgiving week in the United States. I just returned from a 9-day trip to Germany and the Netherlands where I spent time with my mom who is 2 months shy of being 99 years old. This trip came toward the end of a year when I had a successful double heart-valve-replacement surgery.

How far can we push. What can I Iearn?

The Scorsese questions feel especially personal to me in 2023. They prompt me to think of what I am grateful for this year, at a time when our world in turmoil seems in even more turmoil.

Thirst drove me down to the water where I drank the moon’s reflection.”


I love the food part of my American Thanksgiving. Love lounging in bed all morning as the Macy’s Thanksgiving Day parade rolls by on my tv screen.

And I love a bit of quiet reflection time about things I am grateful for.

Chances are, you will be asked to express your gratitude publicly as you gather with family or friends around the Thanksgiving table. Cool. Doing so is a beautiful ritual.

I invite you to, however, find some quiet reflection time of your own. And in lieu of asking “so what I am grateful for?,” consider the following 3 questions as your guides.

These questions are beautifully in sync with Martin Scorsese’s life questions. They will lead you to answers that may be unexpected. They also happen to be perfect questions in times of turmoil or distress.

I think of them as Gratitude 2.0 questions.

REFLECTION #1: What has “moved” me this year?

The word moved is not meant to signify touchy-feely, fluffy, superficial. On the contrary, think of things, situations, people, causes, moments, movements that have stirred you deeply this year. Moved your heart and soul. Ignited your humanity. Know what these things were and are. They are the things that connect you with who you are at your finest. They activate your deepest beliefs and values. They link to your spiritual core, even if it is a core that perhaps operates in hiding behind your rational mind.

Knowing what touches us is a rich gateway to a more authentic expression of ourselves. It is a guidepost to a more impactful way of being and engaging in the world. Self-reflection opens that door. Walk in.

REFLECTION #2: What has surprised me?

The notion of gratitude can feel like we’ll look at only “the good stuff.” Surprise is a value-neutral term. Some surprises instantly feel like “good news.” Others may feel like “bad news.” At times, bad news may, with perspective, feel like “that’s the best thing that ever happened to me.” The surprises may come in the form of unexpected gifts and blessings, amidst a circumstance that we may at first not be grateful for.

I am still surprised that my mom is almost 99 years old. I was very surprised when the need for a heart-valve-replacement surgery presented itself very quickly this year. There are surprises within these surprises. I am most grateful, perhaps, for the learning that has occurred, and continues to occur, within a surprise. I have never been closer to my mom than I am now. Go figure. The surprises invariably deepen my understanding of myself, of another person, the world around me. What a beautiful thing that is.

REFLECTION #3: What am I discovering about life?

Surprises and discovery, at their finest, go hand-in-hand. 2 questions I ask pretty much every one of my podcast guests: What would you like to do more of in life? What less? The answers to these questions are often not easy. They sometimes require that we let go of things and activities that we excel at but have, perhaps, outgrown. That is not always an easy discovery. But how grateful I am when that discovery is made. How freeing it can be to make room for new discoveries and fresh adventures. Yes, grateful.

Gratitude for our successes is a precious thing. So is gratitude for the abundance and love we may know. Celebrate, as well, the discoveries big and small of this year. They are the guideposts to all your potential that has yet to unfold.

This Thanksgiving, carve out some reflection time. Trust that your reflection time will help you to continuously reconnect with your innermost desires and spirit. Know that self-reflection is, indeed, part of every spiritual practice on our planet. Be one of those people that is still growing. Find your inner thirst and quench it.

Drink the moon’s reflection over the holidays. Do so with gratitude and joy.

And if you haven’t seen Killers of the Flower Moon yet, treat yourself and go.

Warm wishes for a peaceful Thanksgiving.

WHY Don’t You Appreciate Them MORE?

Appreciation, Voltaire wrote, is a wonderful thing. It makes what is excellent in others belong to us as well.

Beautiful sentiment.

A no-brainer, right? Yet almost every individual I have coached over the last two decades doesn’t appreciate the contributions of others enough.

Well, let me clarify. They don’t EXPRESS their appreciation enough.

This lack of appreciation-expression is most startling when it comes to how we relate to an authority figure. All sorts of conditioning, explicit or subliminal, about how we behave around folks with power comes into play.

It’s not pretty.

Chances are, you have been taught about “managing UP.” The art of managing a perhaps mercurial, distracted, at times unavailable and often unpredictable boss. If you have worked in the corporate world long enough, you have likely taken a class on this essential leadership skill.

Hint: Know their priorities. Speak their language. Anticipate their needs. Be truthful and don’t BS them. Contract properly at the end of a meeting. Just a few of the essentials.

Chances are, as well, that no one in your class spoke about “appreciating UP.”

You do your best to express appreciation to the folks on your team. You may forget and you may not do it perfectly, but you know that it’s a good idea.

You do, however, little to explicitly appreciate your boss. It’s a potent influencing behavior, and yet, bosses rarely receive a word of praise or appreciation. From anyone. Yes, it’s lonely at the top, in more ways than one.

Here are some of the myths and beliefs that shape how we engage with an authority figure.

3 Boss Appreciation Myths

1. I don’t want to waste their time.

My boss’s time is precious. I want to be prepared, get to the point, and show that I respect how busy s/he is.

Fact: Your boss is a human being with feelings, no matter how efficient her or his outer demeanor may be. The longing for appreciation is universal. Expressing appreciation is never a waste of time. Do not conflate being efficient with not expressing an important thought or feeling – which includes appreciation.

 2. I don’t want to sound like I’m sucking UP.

I’ve watched other people suck up to Senior Leaders and it just looks and sounds so totally obvious. I don’t ever want to become one of THOSE people!

Fact: Even when it looks like sucking up to you, chances are your boss appreciates hearing it. Dump the phrase “sucking up” and supplement it with the phrase “expressing genuine appreciation.” That’s what we’re talking about, after all. If your appreciation is heartfelt, your expression of this appreciation is an act of honest communication. Withholding the comment is an act over unnecessary filtering. You are choosing to be less authentic by not communicating an appreciative thought.

3. My boss is uncomfortable with personal chit-chat.

I don’t want to cross any personal boundaries with my boss or get into a conversation that becomes too private and which I will later regret. My boss isn’t a touchy-feely person.

Fact: Praising someone’s idea, expertise, or accomplishment is as safe as a professional conversation gets. It’s entirely about work. Your story about not getting too personal is likely about your discomfort in offering a personal remark to someone with high position power, not about that person’s discomfort in receiving such a remark from you.

I’m a big fan of Krista Tippett, host of NPR’s consistently inspiring “On Being” radio program. I vividly remember a chat she had with another hero of mine, renowned British poet and organizational advisor David Whyte, about leadership wisdom (Tippett, On Being, 4/7/2016). “Being a leader,” Whyte affirmed to Krist Tippett, “means being visible, all the time. It means truly showing up and not simply going through the motions of showing up.”

Being visible, fully showing up, includes noticing our appreciative thoughts AND having the courage to express them. To anyone. It also suggests we appreciate UP, discomfort and all.

If someone who reports to you offers a compliment or thanks you for something well done, you appreciate it, don’t you? You remember the comment, right?

Act in kind. Express your appreciation, in every direction. That includes UP.

The Line Between TOO OFTEN and NOT ENOUGH

I don’t want to be one of those people who talk too much. Don’t want to repeat what someone else has said. Don’t want to upstage more senior members of the team.

I have heard it all. Reasons why we silence ourselves at an Executive Meeting.

Let’s get this straight: Someone has decided that you deserve a seat at the table at your company’s most senior decision-making body. You ARE a member of the team. And you choose to get coy?

Coy gets you nothing.

Your concerns about mis-stepping in this forum are, of course, valid. You’ve watched colleagues crash and burn when they carry on for too long, over-heat with emotion, and don’t feel the pulse of the room.

Too often/not enough.

Claiming our rightful voice in a circle of power brokers can often feel daunting and elusive.

A flower does not think of competing with the flower next to it. It just blooms."

Zen Shin

He doesn’t always know when to speak up, says Sophie, the French CEO of a global micro-chip manufacturer, about her protégé Massimo as we chat last month. There is a right moment for making your point, and when you miss that moment, it may not come back. Massimo often misses the moment, and when he jumps in, he leads with his emotions, not with strategic clarity.

You may be surprised at just how often the too often/not enough dilemma shows up in my Executive Coaching conversations. Otherwise self-assured individuals crumble in the face of the murky power dynamics of an Executive Team. Most of these individuals err on the side of under-communicating. Their under-communication serves no one.

Consider the following guidelines as you assess what too often/not enough looks like for you in your executive interactions:

Don’t miss the moment.

As the team dives into a topic, as a discussion takes shape, as you feel the urge to state your point-of-view bubble up – notice. Notice the Gestalt of the conversation. Notice the direction of the conversation. Notice your desire to chime in. What are you waiting for?

Wait another 30 seconds or a minute, and a thought that felt right will suddenly seem like a tangent. A perspective that could have shaped the conversation becomes a distraction.

Catch the moment when your instincts nudge you to contribute. Trust those instincts. Jump. Deliver your perspective clearly and succinctly. Then cede conversational space to others.

Silence is not an option.

Occasional strategic silence in a meeting can be a brilliant move. You stay out of the fray. You implicitly allow others to run with the proverbial ball.

Be clear, however: Show up repeatedly in hour-long Executive Meetings without contributing, and you have rendered yourself irrelevant. Whatever your inner chatter tells you about staying silent – ditch it. Your role is not to be a demure quiet presence. Your role is to actively advance productive conversations.

In case of doubt, manage yourself differently. Set a concrete participation goal. I will speak up at least 3 times during this meeting. While this may seem like a somewhat arbitrary goal without context, guess what – you will suddenly find more moments when you can meaningfully contribute. You will have unsilenced yourself. Wonderful.

Be a great supporting player.

No need to always be the star of the show. You know – the one who advances great ideas, fresh thinking, status-quo-challenges. Don’t wish to be that person in a meeting? Cool. You will at times wield greater influence by stepping into the role of robust supporting player. A supporting player validates another person’s suggestion. Expounds on that suggestion with additional data or anecdotal information. Connects the dots between a suggestion and other suggestions in the discussion space.

The supporting player ends up being a bridge-builder. Decision-making-accelerator. This is powerful stuff. We don’t get to play this role by being silent or questioning if we “should support.” No - we just do it.

When a topic is done, shut up.

Each topic has its own life cycle. Intensity of conversation grows. Peaks. Interest fizzles. The group is ready to move on.

Sense the cycle of a topic. Sense the energy that exists in favor of a topic or against it. Don’t be that annoying person who doesn’t know when to quit. Hammers away at a point that has already been made once too often. Doesn’t understand that some things are not negotiable. When you don’t notice the life cycle, you have become the way-too-often person. And the person with way-too-little influence. Notice – and shut up.

Most importantly, understand the decision game in your orbit. Most decisions are NOT made in meetings. They have been made BEFORE the meeting. The meeting is merely a social dance we perform to publicly align around the inevitable. Misunderstand this, and you have abdicated much of your influence.

Want to be part of the pre-meeting decisions? Hold lobbying conversations with key stakeholders prior to a meeting. In these conversations, you will have way more time to advance your point-of-view than you ever get when the Executive Team meets. You will be more thoroughly heard. How cool is that!

Too often/not enough. Now/later/not at all.

That is the dance of the Executive Meeting, isn’t it? The split-second decisions we make, moment by moment, as a team congregates.

Trust your instincts. Don’t over-talk - and know that habitual silence is not an option.

Ever, ever, ever.

How We Foster More TRUST

I have coached my share of “bad boys” and “bad girls.”

Top executives whose strategic endeavors and interpersonal behaviors have persistently pissed people off.

The outcome of such behaviors is always the same. The individuals whose support they need to be successful – their peers and the members of their teams – do not trust them.

The moment folks stop trusting us, we’re on the perilous road to not getting anything done. Or, at best, pushing an increasingly heavy boulder up that mountain. Because in the absence of trust, work gets so much harder.

I was thinking about trust – AGAIN – as I contemplated a 2020 study by the Workforce Institute at UKG, one of the world’s leading providers of HR, payroll and workforce management technologies. The Workforce Institute’s research explored how nearly 4,000 employees and business leaders in 11 countries feel about the state of trust in their workplaces.

The Workforce Institute’s report, “Trust In the Modern Workplace,” is tellingly subtitled Why is trust still hard to find at work?

Here’s the data that grabbed my attention: 63% of all employees and business leaders worldwide stated that trust must be earned. 72% of all C-Suite executives stated it was so.

I’m not upset that you lied to me, I’m upset that from now on, I can’t believe you.”

Friedrich Nietzsche

This, then, is the implied trust paradigm: We hire a new employee because they are hopefully highly qualified. And yet, the majority of us are not sure that we are willing to trust that person. We demand they prove their trustworthiness to us.

This “prove to me I can trust you” mindset is all pervasive but varies by culture, according to the UKG study. It was true for 90% of the respondents from India, 68% from the USA, 50% from Germany, 37% from Mexico.

Is it just me, or does this trust paradigm seem totally backwards?

Here is the framework I find most helpful for understanding what we actually mean when we say I trust you, in a professional setting. Roger C. Mayer, Professor of Management, Innovation and Entrepreneurship at NC State University, calls it an integrative model of organizational trust. It integrates 3 strands:

I trust you implies that I believe you have the necessary skills to do your job well. I believe that you are a person of integrity whose values are in large measure aligned with mine. And I see you as someone who is benevolent – by that I mean you genuinely care about the success of all you work with and the business in its entirety; you’re not merely seeking to climb the organizational ladder and advance your own fortunes.

Do a gut check. This makes sense, right?

Let us assume competence, for a moment. Let’s assume that we honor our commitments. Beyond these 2 c’s, how do we consistently behave in ways that foster deeper trust and unambiguously signal that we can be trusted? Trust signals are transmitted in nanoseconds. This is the tricky part: The specific behaviors can be learned. They will, however, always inhibit trust the moment they come across as fake or rehearsed.

Fake it ‘til you feel it doesn’t work when we seek to build trust.

Here are 4 of those behavioral trust signals. I think of them as Everyday Trust Builders.

4 Everyday Trust Builders

You speak the truth.

Truth is a loaded word, I know. I simply mean this: You have your own bullshit meter. You keep your crap in check. The platitudes. The easy responses. Yeah, they often sound good. And folks can tell when you’re running on automatic pilot. When there are things you can’t divulge, you don’t pretend to be transparent. You acknowledge that there are things you can’t talk about. You stay real even when you have to be strategic. That is speaking your truth.

You shut up.

You invite conversation. In conversation, you let others talk. You listen to the words they say. To the deeper meaning behind the words. You don’t fake-agree. You don’t fake-listen. You give evidence that you have listened AND understood. If you don’t understand, you ask for clarification. You engage with sincere curiosity.

You appreciate.

You appreciate folks at every organizational level. The attendant in the parking garage. The receptionist. The new hire. The accountant who is retiring after 30 years of service. The Head of the Board. Your competitor. Your appreciation doesn’t hide in your thoughts, it is actively expressed. It is expressed not with clichés and platitudes. Your every word and action explicitly show that you have noticed, and that your appreciation is heartfelt.

You are FULLY present.

That means you show up on time. Show up mentally prepared. Show up with heart and mind intact. You don’t pretend to not have feelings. Yes, you show up undiminished, as the whole person that you truly are, beyond the confines of your job function.

We don’t just remember our Everyday Trust Builders on a good day. We remember them on a tiring day, on a frustrating day, on the occasional day from hell. Yes, every day.

The data gathered in the Workforce Institute study makes it clear that there are hidden organizational costs when there is distrust.

Most people long to perform well at work and do the right thing. A palpable lack of trust will invariably inhibit job performance. 64% of all employees said that a climate of trust fostered their sense of belonging. 58% affirmed that it affected their career choices. And 55% stated that it affects their mental health.

You may not be able to affect the trust culture of your entire organization. But you can most certainly choose to foster trust, nanosecond by nanosecond

Be that person. Do it consistently. Do it well.

4 VERY Annoying People. Be Prepared

Of this you can be sure.

No matter where you work, no matter how many decades of experience you have under your belt, no matter how much positional authority you possess, they will show up. The colleagues who trigger the heck out of you.

Annoy you. Provoke you. Enrage you. Keep you up at night.

Well, wait a minute. That is our impulse response.

They WILL keep showing up. We, however, can learn to respond differently.

A conversation I had last week made me think of this. Jennifer was thrilled to join the Executive Team of a red-hot biotech firm 6 months ago. She stepped into a brand-new VP role that had not existed before. The role was created to help the Executive Team get ready for the launch of a highly promising asset 2 years from now.

Great, right? Everyone on the Executive Team had interviewed Jennifer. Everyone had lobbied for her hire. And yet Jim, the Head of Research & Development, engages in continuous public verbal battles with Jennifer. Belittles her. Lobbies caustic comments Jennifer’s way. Or simply ignores her altogether.

When Jim feels bad about his behavior, he calls Jennifer after a team meeting. Apologizes for his behavior. And then continues to behave in the very same vein.

What’s at play here? Personality differences? Organizational politics? Turf wars?

Let’s keep it simple. There are difficult people. Different types of folks are difficult for different sets of people. There are archetypes in the etymology of difficult people. They exist in most every workplace. Their behavior is tolerated for reasons I usually don’t understand. Often having to do with the perceived irreplaceability of a particular individual.

Your job? Notice the TYPE. Don’t take their behavior personally. They’re a type. They can’t help themselves. Notice the type - and have a plan.

Here are the 4 types that most trigger me. As in Jennifer and Jim’s case, they tend to be turf protectors. They are animated by fear.

Let’s look at how they operate – and how to best respond without becoming overly triggered.

1. The Raging Bull

They are wont to erupt unexpectedly in fits of rage and become unglued. This usually comes with verbal assaults on colleagues and team-mates, often while lacking necessary information and without having made efforts to try and understand other perspectives.

What is going on? The Bull is highly stressed, overwhelmed, and afraid of failure.

What can you do?

2. The Competitor

They seem to always wish to surpass you and try to turn every professional situation into a game of one-upmanship. They seek to have the last word in a brainstorm, attempt to upstage in social settings, and at their worst, try to publicly denigrate the value of your contributions.

What is going on?  The Competitor feels, deep down, not as skilled as others, as valued, or as well-prepared. S/he fears becoming irrelevant.

What can you do?

3. The Backstabber

They says nice things to your face, offer compliments and butter you up. You have the impression that they are a trusted friend – until you hear that they been speaking ill of you behind your back and complained about you to “the big bosses.”

What is going on?  The Backstabber resents the attention you’re receiving from folks of influence in the organization. They worry that they will eventually be left in the dust.

What can you do?

4. The Withholder

They don’t share all the information they have with you. They are quiet and incommunicative in meetings – what we commonly label passive-aggressive. They makes you chase them in order to get anything done. Their passivity drains your energy and often wastes your time.

What is going on?  The Withholder feels overlooked and unimportant in the big scheme. And dammit, they won’t put up with it. They will make sure you’re on your own unless you properly ask for their help.

What can you do?

I can get triggered by all 4 of these types. But if I have a fatal attraction, it’s the withholder. Fatal attractions are those folks whose behavior somehow has the power to trigger us faster, longer, more resoundingly. They hold this power because their behavior taps right into our deepest personal wounds.

Disagree with me all you want. Argue with me. Talk behind my back. It doesn’t bother me all that much. The withholder, however, has the power to set me off more than any other type. Why? Well, my dad was a withholder, and even with many years of therapy behind me, folks who withhold can still take me to my personal brink.

There’s only one way forward. Know your types. Recognize your fatal attractions. Have a plan.

When the fatal attractions show up – and they will – choose to not get annoyed. Execute your plan. Stay cool.

That’s where leadership liberation begins.

Are You Helping or Micro-Managing?

Nobody likes a micromanaging boss.

If you have ever worked for a boss who line-edits your written communications or fine-combs your Powerpoint slides, you know.

Eeeek. Aaargh. And yet …

If you are the leader of a sizable team, I feel for you. Taking a completely laissez-faire approach about the endeavors of your team members doesn’t serve them and will likely keep you anxious and wondering. You may quickly become the leader who isn’t actually leading.

What is a helpful rhythm for engaging with your team? Especially if some of your team members are less seasoned than you would like, and you don’t entirely trust their ability to tackle a complex challenge – how do you set them up for success without micromanaging them?

I hire professional staff and then micromanage them until they walk out the door."


A 2021 article in Harvard Business Review - How to Help (Without Micromanaging) by Colin M. Fisher, Teresa M. Amabile and Julianna Pillemer (HBR January/February 2021) – got me thinking about this perennial dilemma. The authors hail from University College London’s School of Management, Harvard Business School and NYU’s Stern School of Business. They have spent the last 10 years studying how effective leaders offer help without micromanaging.

Their research suggests 3 specific strategies will help you to be a hands-on boss who doesn’t micromanage:

  • Time your help so it comes when people are READY for it.
  • Clarify that your role is to be a helper.
  • Align the rhythm of your involvement – its intensity and frequency – with people’s specific needs.

Reads nicely, right? In my experience as an Executive Coach, this is not as easy as it sounds. Helping well requires situational astuteness and finesse. And the ability to slip in and out of different ways of inhabiting your leadership role.

How To Operationalize Being Helpful

1. Make HELPING Part of the Lingo

Talk about the notion of helping others to be successful. Make it explicit. Explain that help comes in many forms and moves in many different directions. Demonstrate that you are not a know-it-all boss or the smartest person in the room. Talk about how you receive help – from your own boss, from a coach or an advisory team. Show how asking for help and receiving help are not a sign of weakness.

Approach your team members for help when they may be able to do so. Live the famous Steve Jobs quote: It doesn’t make sense to hire smart people and then tell them what to do. We hire smart people so they can tell us what to do. These are all ways in which you create a culture of help where you helping your team is just that – HELP, not micromanagement.

2. Be in Relationship More Frequently

Think of venturing beyond the traditional “standing 1:1 meeting” with a member of your team. You run the danger of having a predictable if unexciting work cadence with this team member - and then you suddenly swoop in and hover in the midst of a perceived crisis. Anxiety levels rise, as do the possibilities for micromanagement.

Most of the executives I support opt for a different engagement style with their team members. More frequent short calls. Impromptu, unscheduled. Texting. Just to say hi. The chat can be about work or personal matters. 10 minutes or less. The intent is not to check up on your team member. No, you choose to stay in relationship. The relationship is informal and unforced. Needs for help and support have a forum to easily emerge. They have a place where they can come forth in a timely manner.

3. Do NOT Help Preemptively

You mean well. Your team is about to embark on a critical project, and you want them to be prepared for everything that might derail things. You gather for a meeting, and you “lay it all on them” in this meeting. Cover all potential scenarios. You let the team know what you have done in the past when “things went wrong." You shower your team members with tips and advice. You’re proud of how pro-active you are.

You think you’re helping. Please note: You’re helping when no help is needed yet. You have created alarm when no alarm has sounded yet. You’re micromanaging before any of this micromanagement is possibly warranted. Thinking of potential challenges can be helpful, of course. Let your team drive this conversation, not you. Otherwise, it is more likely a case of your Ego running amok. Stop.

4. Contract Your HELP with your Team Member

If you notice that in the midst of a project one or several team members are struggling, resist the urge to swoop in and take over. Consider a more collaborative approach. Tell your team members what you observe and brainstorm possible ways of addressing a challenge or bottleneck. Make it a “together” conversation.

If you have an idea for getting involved in a hands-on way, propose it. Be clear about the depth of the involvement you propose and the length of it. Test to see if the idea of your help resonates. Chances are, your team members will feel a bit of inner pressure to accept your help. Understood. When they do, however, you have established explicit boundaries for your help. You have consciously contracted. And you have not become the jerk-boss who took over because, well, you could.

The urge to help is primal, universal and timeless. It’s a wonderful urge. Honor it. But please get your Ego out of the way. Be clear that, at times, helping might mean allowing the other person to learn from making a mistake. At other times, it might require some in-the-moment coaching. Or sending a team member to a training class. Hovering is not help. Constant correction is not helping.

Go and help well. If you have any inclinations toward micromanaging, notice how much more enjoyable it is for you to lead without doing so. Notice what a relief it actually is. And how much more appreciated your leadership is.

Be relieved. And manage your urge.

Lean Into CONFLICT a Little More, OK?

It happened last week.

Javier and Natalia, Heads of separate business units in a biotech firm, are collaborating on a project. Javier has prepared the monthly Powerpoint update for the Executive Team. He’s partnering with an external vendor who has given the slide updates a sleek, polished look. Text has been reduced to minimal bullet points.

Javier is thrilled.

The day before the presentation, Natalia – who has been mired in non-project fire-fighting and had no time to hand in her slide content – submits the information she wants included in the deck. Natalia’s additions are unwieldy, wordy, way too detailed. They do not mesh with the presentation that was just created.

Javier is enraged.

And it’s not the first time Natalia has enraged him.

Conflict cannot survive without your participation." 

Dr. Wayne Dyer

We all have different inclinations about how to act in such a situation. The Thomas-Kilmann Inventory (TKI) is the best known analytical instrument that delineates most individuals’ preferred conflict-engagement styles. According to the TKI, there are 5 major human tendencies when we find ourselves in conflict with others. There is avoiding conflict altogether. Accommodating the other party. Competing. Compromising. And collaborating.

I have already tried to collaborate with Natalia, Javier may think to himself. She’s completely unavailable.

Rage. More rage.

I’m not here to tell Javier what to do. If you’re a competer, you’re likely to exacerbate a dilemma and not resolve it. If you’re prone to avoiding and accommodating, you’re likely to fuel that rage. And if you lean toward compromise (that thing Mom and Dad instilled in us as the always desirable outcome), you’re likely to feel deflated and unhappy, most of the time.

Let us consider another path, shall we! It is predicated on the belief that habitual avoidance never works. And it affirms that conversation is invariably a good thing. 

5 Tips to Lessen Our Conflict Avoidance

1. Don’t call it conflict

Labeling a conversation as “addressing a conflict” is loaded. So, unload your conversation. Semantics matter. Unload it from this label or equally charged synonyms. You’re not here to have a difficult conversation. A crucial conversation. A showdown. Overcome a challenge.

No. You’re simply meeting to share your perspective on a matter or situation. You are doing so to open the door to a conversation. You’re also interested in learning about the other person’s perspective. Bottom-line is, you’re simply having a conversation. That’s it.

2. Prepare for the conversation

If the situation you plan to discuss with your colleague makes you nervous, has caused you anxiety or invoked obsessive thinking, it may be helpful to write down in advance what you wish to say in this conversation. The act of writing tends to immediately calm us down. It helps us think of the simplest, cleanest, least verbose way of expressing what’s on our mind. We are literally gathering our thoughts. And we’re likely catching any language that might sound inflammatory in the conversation.

Important: Just because we wrote it down doesn’t mean we have to “cling to the script.” Trust that the right words will be uttered in the moment, informed by the preparatory writing you did.

3. Use an I-Statement

An I-Statement is the simplest, cleanest and most powerful way of saying something that feels hard to express. Here is the structure of an I-Statement:

Were Javier to use an I-Statement with Natalia, it might go something like this: I get very frustrated when you hand in your materials at the last minute because it causes us to totally change something that several of us have worked hard on and necessitates hours of additional work.

The key to a successful I-Statement is that we deliver it calmly. Voices are not raised. Because the statement focuses on OUR experience, it is hard for the other person to argue with an I-Statement. The beauty of the third leg of the statement is that it invites other persons to think of the impact their behavior has on us – something they likely had not contemplated up until that point.

4. Listen to their story

This is often the most difficult part in any conversation, especially when we feel slighted by someone, mistreated or misunderstood. We want to keep talking and talking and talking until we know that they GOT IT.

Stop. Shut up and listen and allow the other person to tell you about their challenges and frustrations. It’s really not that hard. Stop talking. Choose to be curious. Listen. You don’t need to agree or disagree with anything in this very moment. Don’t need to argue or rebut. Simply stop talking and listen.

5. Don’t force an outcome

You may be entering the conversation with a very clear notion of the 3 action items that would instantly solve a current dilemma. You know exactly what things you want the other person to do differently. You’re itching to say Look, here’s what I need from you. Got it?

You’re allowed to ask for those things. But why not simply allow a potential outcome to come from the other person? What might we do differently going forward? is a powerful question. It’s not What can YOU do differently? (potential attack). The we-version is collaborative. It invites a path forward; it doesn’t force it. And when the path comes from the other person, s/he is way more likely to commit to it.

The ultimate non-forcing? It has been drilled into us that a conversation needs to end with action outcomes. Perhaps what was needed, in this particular moment, was just the conversation. More time to think. Another follow-up conversation, perhaps. No forced outcomes. How liberating is that.

It’s not that hard. It really isn’t.

We’re merely having a conversation. Drop the narratives in your head that heighten the mental drama around this conversation: We’re resolving a conflict. We’re having a difficult conversation. This will be a showdown.

Drop ‘em.

We’re simply having a conversation. I’m here to share my perspective and listen. I will do so with a measure of skill and hopefully kindness.

That’s it. There may actually be no conflict. Go figure.

6 Keys to Being a Better Collaborator


I’m often NOT a good collaborator. Sometimes, I’m a horrible one.

I was reminded of this during a chat last week with my colleague Vera, Head of HR for a global life sciences enterprise.

I love to collaborate with you if respect you and your skills, I confess to Vera. If I don’t, all my worst instincts come to the fore.

Sigh. From me, from Vera.

I know, she says. Collaborating with a bunch of A-team players can be exhilarating. Most of the time collaboration feels like a complex and never-ending slog to an outcome you don’t love, and you wish you had just done it by yourself.

Another sigh. It felt good to own it.

Collaboration is one of our workplace sacred cows. We’re expected to embrace it as a rollicking good practice. The challenge, says Francesca Gino, a professor at Harvard Business School, is this: Leaders who want to create collaborative workplace cultures try hard to instill collaboration as a value. What they forget is that collaboration requires good old-fashioned skills. More importantly perhaps, subtle and highly nuanced skills. The sort of skills that we hone through a commitment to life-long learning.

Collaboration is the essence of life. The wind, bees and flowers work together to spread the pollen."

Amit Ray, Indian author and mystic

Gino’s article in The Harvard Business Review – “Cracking the Code of Sustained Collaboration” (HBR, November/December 2019) – highlights the work of companies such as Pixar, Webasto, and American Express who invest in collaboration-skills-training.

When I look at the list of 6 skill sets that Gino identifies, my first thought is yeah, I know these. Upon reflection I remember how “not easy” they are – and how quickly they can fly out the window when we collaborate with someone who for whatever reason is not our ideal collaborator.

Let’s take a look at Gino’s top 6 collaboration skills.

1. Teach people to listen, not talk.

But of course, you may say to yourself, I have taken an active listening class. Well, here are some very specific ways of practicing a higher-level of listening, especially when the conversation may not be flowing with ease:

2. Train people to practice empathy.

When I was trained as a mediator at the Brooklyn Courts, one of the most potent techniques I learned was the “Shoe Swap.” Instead of rebutting what a speaker says, I intentionally pause, put myself in the other person’s shoe, for just a moment, to sincerely seek to understand why s/he thinks or feels the way s/he does.

Hard to do. And powerful stuff. It invariably changes the course of any conversation.

3. Make people comfortable with honest feedback.

Because so many of us have received vague, platitudinous or at times personally hurtful feedback, it is easy to shy away from giving honest and actionable feedback to others. Or we may, intentionally or not, signal that we don’t wish to receive feedback ourselves and just want to get on with things.

How do we begin to move into a more effective feedback environment that prevents collaborative endeavors from getting stuck? Have the courage to openly talk about aversions to feedback, choose to practice frequent feedback that is direct, specific, and actionable – and give each other feedback about the quality of feedback that is or isn’t happening. Stay feedback-conscious!

4. Teach people to lead AND follow.

I have taught these skills for years. Some folks call it switching from Advocacy to Inquiry. I like energy language and think of it as knowing when to Push and when to Pull.

Great collaborators are comfortable with both pushing and pulling. They have a keen sense of when to use one approach over the other. And they do so with clear purpose. Makes sense, right? The key success factor: Be comfortable with both communication styles AND use them with strategic intent.

5. Speak with clarity, avoid abstractions.

Know when brainstorming is over. Know when abstraction, more big ideas and additional data will not move you closer to action or making progress. Know when it is time to get specific. Know when it is time to condense what you need to say into 3 or 4 sentences. Know when it is time to call for action. And have the courage to do it. You will elevate the collaborative discourse for everyone involved.

6. Train people to have win-win interactions.

Sounds good, right? You may even have studied the terrific Harvard Negotiation model that teaches tools for getting to win-win. In reality, this is never easy. If I had to boil a win-win mindset down to 2 simple tactics, it is these:

Since I am quoting wisdom from a Harvard Business Review article, allow me to quote one more HBR article. If you’re collaboration-weary, you’re not alone. In “Collaboration Overload” (HBR, January-February 2016), authors Rob Cross, Rebele and Adam Grant asserter that in the last 2 decades, the time spent on collaborative activities in a corporation has ballooned by 50%.

Moreover, their research shows that up to a third of value-added collaborations come from only 3% to 5% of employees.

These findings pinpoint what you already know so well from your own life. How often have you been invited to a meeting where you were not critical to a collaborative endeavor – yet, there you were? How many other folks were sitting in the same meeting who also were not essential to the same project?

Collaborate when collaboration is essential to a project’s success. Be clear when true collaboration is NOT mission-critical. Avoid collaboration overload.

And if you’re going to collaborate, do it with skill.

Connecting With The Transactional ALPHA Exec

You dread your meetings with Mitch.

Mitch is 100% transactional. All business, all the time. You feel rushed when you speak with Mitch. And you don’t know how to stop the alpha-train.

Worse yet, you’re a person who values relationships. You know that everything in business works better when you have built a rich relationship with a colleague. A reciprocal business relationship energizes you.

Nothing about Mitch indicates that a relationship matters to him. With you, or with anyone else. Mitch just wants to “get it done.”


I found myself thinking of this challenge a couple of weeks ago when I was delivering a Master Class on Influencing Skills. Building authentic and sustained business relationships - I trust this intrinsically makes sense - is a key influence lever. More influential folks are more adept at developing key stakeholder relationships.

How do you build a relationship, I was asked, with someone who is not interested in relating?

If only you could sense how important you are to the lives of those you meet. There is something of yourself that you leave at every meeting with another person.”

Fred Rogers

It’s a challenge. We tend to talk about hitting this wall in terms of better understanding personality differences or adapting our communication styles. This, however, is a more fundamental dilemma. How do we connect with someone who does not seem to value connection?

Let’s begin here:

  • Don’t try to stop the alpha train.
  • Accept that you will not have a great relationship with everyone.
  • Learn to love what is.
  • Focus on Mitch’s assets, not his liabilities.
  • And – drum roll, please – do not give up on the possibility of connecting. Because psychological evidence shows, over and over again, that no matter the personality type, no matter how “closed” a person may seem, the longing to connect runs deep. Connection is why we’re here, Carl Jung wrote. It is what gives purpose and meaning to our lives.

Consider the following tips as you engage with a highly transactional alpha executive. Think of them as your “disarm them” tool kit.

4 Ways To Disarm a Transactional Executive

Meet them where they are.

Don’t force the small talk. Don’t chatter about what you and your family did over the weekend. Don’t ask her or him what they love to watch on Netflix. Let go of your preferred way of connecting, just for the moment. Make peace with transactional, because transactional is just fine.

Reframe transactional, for yourself. Transactional need not be cold, formal, unpleasant, or difficult. Transactional is focused on completing a transaction. And completing a transaction, beyond the human connection lens, can be mighty satisfying. So, relax please.

Connect around the present moment.

Instead of bringing extraneous stories into a conversation, notice what’s happening in the present moment. If there’s a thunderstorm brewing outside of your window, mention that. If there is a vacation photo on your conversation partner’s desk, inquire about that. If there is a beautiful painting on the wall behind your colleague, acknowledge it. These are simple and safe ways to initiate a human moment that is not forced. And your prompts may invite the other person to share more.

Gina, a Corporate Comptroller, described one such moment to me. I was on a Zoom call with my international team. Some of them I have never met in person. Archie from the UK was wearing a sweater that had this goofy design on it. I was chuckling to myself, inside, as I noticed Archie’s sweater. I wasn’t sure if I should comment on the sweater or say something cute.

If Archie wears a goofy sweater, Archie wants you to notice the sweater. It’s almost rude to not acknowledge the sweater. The sweater is literally staring you in the face. It is present-moment-reality. And acknowledging the sweater may well prompt a fun story or two.

Connect around work history.

If you sense that a colleague does not wish to get into “personal stuff,” go deeper with the business content. When you are trying to solve a problem or need to make a decision, open the door to the past. How have you tackled this in the past? What was the biggest challenge you faced last time this happened? What did you learn in previous times that we should consider today?

Questions about past experience are safe. They explicitly acknowledge the other person’s experience and expertise. They will always expand a conversation and may elicit an unexpected story or insight. All wins.

Celebrate them.

Successful people rarely receive enough compliments. Here’s one thing I hear in my Executive Coaching practice all the time when we talk about paying a compliment. It always startles me. Well, I don’t want to sound like I’m sucking up to her.

Please be clear – this is your crap about giving and receiving compliments. Drop it. If you find yourself in a fast-moving transactional conversation and the other individual says something genuinely helpful or insightful, please acknowledge it. That was so helpful, Mitch. I never looked at it this way before, Mitch. Thank you for helping me look at this situation differently, Mitch. I appreciate how you analyze a difficult situation, Mitch.

Don’t say it if you don’t mean it. If you mean it, DO say it. Your comment may well open the door to a much richer conversation than you thought was possible.

Sometimes our light blows out, the theologian and philosopher Albert Schweitzer famously said, but is blown again into instant flame by the encounter with another person.

Think of the possibility of connection as one of those instant flames. Respect the other person’s conversational limits and personal boundaries. Do not force yourself on her and him. At the same time, remember that the simplest statement from you has the power to ignite the flame.

Stay in the moment. And light the match.