Before You Say Yes: Negotiating with a Visionary Executive

If you’re lucky enough to work for a visionary executive – one with a clear sense of direction that inspires bold ideas – you’re used to being asked to implement ambitious new initiatives on tight timelines. If we admire or fear these charismatic leaders, we’re inclined to say a quick and hearty yes when they ask us to take on heroic tasks. Only later, when we realize the impossibility of what we’ve signed up for, do we wish we’d asked more questions. Discouraged, we may start ignoring their project, hoping our executive will forget. More likely, they’ll call a few months later, angry that they’ve seen no progress.

What’s more, it’s disrespectful to commit our teams with no due diligence. We know their capacity and mustn’t overload them when they’re already hard at work on other tasks that support corporate strategy (and likely our executive’s prior inspirations).

Your team wants to add value, and they count on you to direct them to their highest and best use, even as that changes in response to shifts in the external environment and your leaders’ evolving understanding of the best ways to compete. Your executive, likewise, needs to be able to count on your commitments. That means you need to learn (and share) enough in these conversations to get to the yes that’s best for your executive, your team and the company.

Here’s a collaborative and thoughtful way to engage when a visionary executive asks you to make something happen.

  • Understand the vision. Assume your executive’s vision is reliable. What is he seeing? What is she excited about? Ask questions with the intention of getting a better look inside their head.

Tell me more about what you’re imagining.
What will this enable us to do?
How does this help us compete?
How big a deal is this for us?

  • Learn about the urgency. Why is your executive talking about this idea now? Why is this the right time? Which projects underway might this new one be replacing?

How quickly do you imagine this happening?
What’s driving this initiative?
How urgent is this?
What’s at stake for us?

  • Share the enthusiasm. As you get a clearer picture of your executive’s vision and sense of urgency, express genuine excitement about whatever you find genuinely exciting. Don’t worry yet about practical questions of how to get things done. You’ll be headed there shortly. Affirming the good your executive is trying to do sets up a fruitful negotiation about what happens next.

This would put us way ahead of the competition.
I love how this makes great use of all the competencies we’ve been building.
Our customers would love this.

Having understood and joined the vision, you’re ready to speak for front-line reality. You usually know your team’s capacity better than senior leaders do, and they count on you to manage it wisely. As you pivot to this part of the conversation, you might find it helpful to say something like

Let me get with the team and figure out how quickly we can make something happen.

This statement is a yes, but it’s a smart yes. It’s an agreement to take seriously the executive’s vision and desire to make it happen. It’s also a commitment to accept the executive’s urgency and move quickly. It is not, however, a commitment of your team to deliver the full vision.

Now you’re going to ask, on your team’s behalf, all the questions they’ll be asking you when you describe the executive vision and ask them to work on it.

  • Which aspects of this project should we prioritize?

If we take on this project on with the time the team has available, which pieces should we prioritize?
If we can do some of this right away, what would you like to see first?

Here you’re offering to devote available bandwidth to the project and asking your executive to prioritize deliverables. This question will often help surface their real driver. Yes, they may see exciting promise in a new communications platform, but you may discover the pressing concern is getting the board online for a monthly meeting. If they insist on your taking on the entire project they’ve described, move to the next question:

  • What could we deprioritize?

To get your team time for this project, you’ll have to put something off. Invite your executive to make that call. Negotiate the bandwidth needed to deliver what they’re telling you is the new priority. Of course, you have to defend other executives’ projects! Don’t let your visionary exec bump what you’ve committed to their peer.

If your executive won’t let you deprioritize anything, ask:

  • Where can we get the extra resources we’ll need?

Let your executive know what it would take for you to add another project to your roadmap. If they won’t authorize additional resources, you’ll need to be courageously clear.

  • This will put other commitments at risk.

I don’t see how we’ll do it, but if you insist, we’ll try.
Here’s what I expect we’ll be up against.
Here’s how I plan to deprioritize if we have to…

Before you say yes, you have to make sure you highlight the risks involved. If your executive cannot accept additional risks on projects already underway, then you’ll go back to suggesting ways to scope down the initial project, deprioritize projects or get extra resources. Unless you’ve missed something your executive is seeing, these are your only options.

These conversations can feel tough and courageous in the moment. You must be centered and generous. This is not a battle of wills. You are on your executive’s side. You support the vision and want to help build it. You’re also protecting work in progress, much of which is helping realize your executive’s other good ideas. If you graciously represent the real constraints of limited resources, you’ll be helping put solid ground under your executive’s vision.

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A Philosophy of Stage Fright

Years ago, I went to my mentor for help with anxiety about an upcoming presentation. I’d had a conversation about the spiritual power of money with an acquaintance, a well-connected businessman, and he’d invited me to give a talk on the topic to his colleagues at work as part of their lunchtime speaker series. As the day drew nearer, I descended into dread, imagining all the ways I might make a fool of myself.

My mentor asked: “Why do you want to help these businesspeople?”

I didn’t understand the question. “They’re important, and I need to look credible.”

“I see,” he said. “So, you intend to impress them.”

“Of course,” I said.

“Then you’re going to be anxious.”

Stage fright, it turns out, is mostly a spiritual condition. When we intend to impress someone (or satisfy or survive them) we make an object of that person; that is, we perform to get what we want from them — applause or praise or a job or a date or some signal that we’ve pleased or appeased them, that we’re acceptable. With this narrow goal comes the risk of failure and the anxiety that blocks real connection.

Somewhat mysteriously, a speaker’s intention actually changes his audience. People sense when someone wants to impress them, and they usually play along: If our speaker expects a review, we become critics. “We teach people how to treat us,” says Wayne Dyer. In this sense, stage fright is a self-sustaining economy. A speaker who wants to impress teaches the audience to be the judges she fears.

My mentor asked again, “Why do you want to help these businesspeople?”

“I don’t know,” I said. Because I didn’t.

“What do they need?” he asked.

“They’re very accomplished, powerful people.”

“They certainly don’t need you to impress them,” he said flatly.

“I don’t think of them as needing anything.”

“But what if they do?” he said. “What if that’s why they invited you? Are you willing to help them?”

The willingness to help almost always crowds out the drive to impress. In that respect, generosity is the opposite of anxiety. My guide was offering me a more powerful intention, one in which I joined my audience or even helped them connect with each other. Rather than trying to get something, he was inviting me to give.

He was also inviting me to trust — to trust strangers, how they might respond, and what might come of a genuine connection that I didn’t control. I wasn’t ready for that. So I filed his advice, and a smaller, greedier part of me set out to conquer my nerves so I could successfully deliver.

The day of the event, I was pumped and confident. My points were polished. When the talk ended, the executives applauded politely. I had apparently met their expectations. On the way out, I saw disappointment on the face of the man who’d invited me.

“That was good,” he said.
“What was missing?” I asked sheepishly.

“I wish it had been more like when we talked,” he said. “I wish they could experience that.

Later, I told my mentor: “I decided to impress them.”

“So you performed.”

“It wasn’t effective,” I admitted.

“It wasn’t kind,” he said.

These days, I help others work with stage fright. Most of them have tried the technical solutions — beta blockers and deep breathing and affirmations. We work on the spiritual angle.

A Wall Street executive called for help with a tough presentation.

“What makes it tough?” I asked.

“I’ve got to talk about something that’s not important with people I don’t like.”

I remembered my mentor’s words: “To talk about things that don’t matter is to practice despair.”

“I can help,” I heard myself say, “if you can manage to care.”

One financial expert told me public speaking made him feel like a fraud. I asked what his audience was afraid of and why they needed what he knew. Over the next few weeks, we practiced techniques for organizing and sharpening his points. Throughout each day he’d remind himself: “I am willing to help.” Gradually his anxiety dissolved. I called him a few months later to see how things were going.

“I miss stage fright,” he said. “I had a great excuse. Now, I just have responsibility.”

What if stage fright is simply excitement about the difference we might make — a difference that’s rarely about us and never about our egos? The real difference is what happens when we risk seeing each another, and we risk seeing when we’re willing to share.

What difference could you make if you weren’t afraid?

Are you willing to help?

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Silence is What Trust Sounds Like

A technology business recently asked me to listen to recordings of their salespeople “cold calling” prospective customers. On each call, a salesperson was speaking with someone at another company, someone they didn’t know, hoping to interest them in learning more about the technology. In some cases, the customer would agree to introduce the salesperson to others in their company or set up a meeting with decision makers. The technology business asked me to figure out what made these calls successful — that is, what about the salesperson’s approach helped a customer come to trust her enough to risk inviting her in?

Listening closely to the calls, three patterns stood out. First, the more often the conversation passed back and forth (with no one speaking for too long at one time), the higher the probability that the customer would say yes. Second, on successful calls, the salesperson was asking more open-ended (fewer yes-no) questions. Finally, the salespeople on successful calls talked more about the customer’s problem and less about their own solution.

On most calls, however, the salesperson did most of the talking, asked a lot of yes-no questions (as if they were troubleshooting instead of trying to learn), and was quick to pitch the features of their technology. These calls were almost never successful and almost always painful to listen to.

So if shorter statements and quicker handoffs, open questions, and focus on a shared puzzle make for better connections, why weren’t the salespeople (whose bonuses depended on building this relationship quickly) doing these things? Why, even when we demonstrated the more effective practices, did they resist changing their habits?

Like most of us, their actions expressed their faith. They were doing what they believed worked. As I coached these salespeople, they taught me how they understood customers:

“Customers are busy, so you have to talk fast and make all your points before you lose them.”

“Customers get lots of calls, so you have to sound smarter than the other salespeople wasting their time.”

“Customers are suspicious; they won’t tell you anything about their business until they see what you have to offer.”

“Pause after you make a point? But what if they don’t say anything? Silence is awkward!”

“Open-ended questions? But they could say anything! I could lose control of the conversation!”

The salespeople assumed they knew how the world works. That’s why they wouldn’t risk changing their habits.

The best practices we saw in the sales conversations illustrate my grandmother’s favorite proverbs.

She’d say: “One point is a conversation. Two points is a speech.”

And: “You make people smart by how you listen to them.”

And, “Silence is what trust sounds like.”

This wisdom runs counter to our habits and challenges grounding (usually unspoken) assumptions about what makes us likeable, acceptable, useful and safe. And yet, almost as often as you’re willing to test it, the wisdom proves true.

In the workshop, we gave the salespeople a chance to role-play conversations with the new rules of engagement – one point per turn, open questions and focus on the puzzle, not the solution. At first it was difficult and uncomfortable. Then it got easier. Then fun. Then they began to imagine engaging customers in these more hospitable ways.

Then we sent them off to experiment on their sales calls where they almost always got better results. Later when we debriefed, the salespeople sounded a lot like new converts:

“If you’re really listening, people want to share!”

“Silence is where people make discoveries and decisions.”

“If you’re willing to learn, people will teach you how to sell to them.”

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Deeper than Division: Questions for Hard Conversations

This year friends have invited me into some difficult conversations on the issues that divide neighbors — discussions about guns, immigrants and sexuality. Some of these conversations took place in churches, others around dinner tables.

The most interesting conversations, the ones that seemed to get somewhere, got underneath what we believe to the deeper issues of how we believe and why.
I started paying attention to the questions that were helping us have the conversations we really needed, and in most cases these were questions not about issues but about us.

Here’s a list of questions (in no particular order) worth inviting into your next tough discussion:

– What do I bring to this conversation?
– Why does this question matter to me?
– What does this question mean to me?
– What comes up for me when someone asks this question?
– What makes this conversation difficult for me?

– What experience do you bring to this conversation? When has this topic been personal for you?
– How did your opinions and convictions on this subject take shape? What formed you on this topic?
– What other experiences to you imagine people are bringing to the conversation?

– What is at stake for us in this conversation?
– Where in conversation about this question do we have the opportunity to love one another?

– How is this question different from other questions?
– What other questions are like this question for us? What do they have in common?

– What are we afraid could happen in a conversation about this topic?
– What do I hope could happen in a conversation about this topic?
– How might we best prepare to discuss this question?
– What rules of engagement might help us with this conversation?

– Who else is struggling with this question?
– How might we be present with the broader community as we converse together?

– To what extent have we identified with a “side” in this discussion?
– What do we most respect about the other side?
– What about our own side makes us most uncomfortable?
– What sorts of shared value or common ground do the sides share?

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Avoiding Interrogation

To find the opportunity with a new customer, you’ve got to make yourself teachable.

You’re not teachable if you’ve already decided what the opportunity is. You’re not listening if you’ve already decided what the customer should buy or fixed on what you want to sell them.

If you’re asking lots of yes-no questions, testing them against some pre-determined hypothesis, you’re probably annoying them.
No one wants to be qualified for your solution before you’ve really understood their business and what they’re trying to do.

Closed-ended (yes-no, fill-in-the-blank or multiple-choice questions) make a customer feel diagnosed and interrogated.
In initial conversations, customers prefer open-ended questions — what, how, who and why — questions that invite them to share perspective and tell their story. Thoughtful open-ended questions build a relationship faster.

If you’re used to troubleshooting, it will take practice to pry open your closed questions, but it’s worth it. You’ll quickly discover that the open-ended versions are the quicker route to the sale.


Are you using automated tools to track your inventory?

How big is your IT team?

Would you like to spend less time on maintenance?

Is [Competitor] working out for you?

Are you having trouble with X?

Are you using Windows or Linux?


How are you tracking your inventory now?

Who manages your system today?

What do you want your IT people to be doing?

What do you like about [Competitor]?  What else would you like it to do?

How do you manage X?

Tell me about your OS.

You can convert any yes-no question to a friendlier open-ended version by assuming the answer to the original question is “yes” and asking the follow-up question.

Instead of…

Are you going to add capacity to
your data center?

Try this…

How do you plan to increase your capacity?

Yes-no questions are particularly annoying when they’re leading — that is, when you’re using a question to express your point of view. You’ll usually get better information by stating the point directly. Provocative statements encourage customers to ask questions.

Instead of…

YOU: Would you like to automate that process?

Try this…

YOU: A lot of our customers get big savings from automating that process.
CUSTOMER: How do they do that?

If you really want to annoy a customer, ask multiple questions at once: “Are you having thermal issues in your data center? Any hot spots or trouble controlling airflow or issues like that? Would you say that’s been a problem?”

Compare that with this version: “How’s the temperature in your data center?” Full stop. You’ll get a much better response from customers when you ask one question, then be silent and really listen to their answer.

If you’re listening, the customer will keep trying to teach you how to sell to them.

Sometimes customers do that by giving you an incomplete clue, something that sounds promising but isn’t explained. Take the bait. Always prompt them for more:  “Tell me more about that.”

CUSTOMER: This approach to storage would connect well with our new XTR initiative.
YOU: Tell me more about that initiative.

When a customer uses a vague, general term or a buzzword — flexible, interoperable, scalable, user-friendly, consolidated, streamlined, integrated — always ask, “What do you mean by that?”

CUSTOMER: This solution has to be very flexible to work for us.
YOU: What does flexibility mean for your organization?

CUSTOMER: We’re trying to make this scalable.
YOU: I’d like to understand that better. What does scalable mean for you?

Opportunity hides behind buzzwords.

Don’t interrogate customers. Engage them. As you ask open questions, make provocative statements and follow clues, they’ll teach you their business. You’ll see which of your messages are relevant. You’ll learn how to express your value in their language.


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On Differentiation

How do you differentiate your offering in a fiercely competitive market?

How do you demonstrate the difference that matters to your prospective customers?

As competition intensifies in your space, it gets harder to differentiate your product.

Unless you’ve got a defensible patent or copyright or trade secret, your competitors will be copying your features and functions as fast as you come up with them.

Particularly in the market for sophisticated software and technology products, customers may struggle to understand exactly what products do or how they work. When customers lack relevant expertise, your competitors can easily claim that their products do whatever yours do — “We’ve got a big data set. We’re fully interoperable. We do cutting-edge analytics.” And so on. Any “differentiators” you can list as bullets on a PowerPoint slide won’t set you apart from rivals who will simply cut and paste. Customers confused by competitive claims either go with gut instincts (which often work against you) or pull back.

In markets where you can’t definitively differentiate your products, the challenge is to differentiate the partnership you’re offering customers, to show customers some unique promise of working with you to solve their problems and grow their business.

Of course, you don’t prove the value of a partnership by talking about it. Your competitors will also claim to be “trusted advisors.” But customers judge a partnership by the experience they have working with you — and that work begins with your first sales call.

Customers listen for your perspective. Behind your marketing materials, features and functions, what do you know about their business and their challenges? They aren’t really interested in how your technology differs from your rivals’. They want to know how your approach to their problem can help them do business differently. So they wonder: How deeply and broadly do you understand the puzzle they’re trying to solve? Do you understand how they’ll actually use your solution and how it fits with their other solutions? Do you understand the goals and concerns of all the people affected?

It’s important to understand the point of view your competitors are bringing to customer conversations so you can tell customers, “We see it differently.”

More critically, can you offer insight, a fresh way of thinking about their problem, an aha! moment? This insight often comes in the form of a better question than the one the customer is asking, a question that reframes the problem and switches their point of view, a question that points at root causes or hidden connections or bigger issues. (Remember, if the customer were asking the right question, he would have already solved his problem.)

When the customer experiences insight in a conversation with you, when they’re digging beneath their current understanding to something deeper, they decide that you understand the puzzle better than they do. They begin to trust your judgment and see value in the partnership. They trust you with information that will help you build a value proposition and make a sale.

When you understand the problem and potential solutions better than your competitors do, you can have a conversation they can’t have — and that differentiates you.

A prospective customer is also trying to discern your guiding principles — how do you work with partners? How do you learn and innovate and create value? Seeing your principles in action helps them judge the promise of partnership.

Are you genuinely curious and interested in their business and in the puzzle they’re trying to solve? Again, it doesn’t really matter what you or your competitors say about your principles. The questions you ask and how you listen and what you do with the information they share shows customers how you do business. Genuine interest differentiates you from competitors who would rather do all the talking.

Are you empathetic and understanding? Do you get what they’re trying to do and why it’s hard? Do you really understand where they’re stuck and why they haven’t been able to solve the problem themselves and what it might take to get them over the hump? This ability to learn quickly and connect with their concerns will distinguish you from the crowd. It’s a critical differentiator in markets for complex software and technology solutions.

When you engage a customer with curiosity and empathy, when you’re humble and generous in conversation, you’re modeling an approach to consultation they can trust. They experience your respect for them and their expertise (after all, they know their business much better than you do) and your intention to create value in partnership. They see you giving them their rightful role in the partnership, and they will teach you how to sell to them.

Finally, you can differentiate yourself through your protocols and practices. You build trust by showing up reliably, by anticipating their questions and concerns and communicating clearly. A prospective client is always wondering: How easy would you be to work with?

So when a customer asks: How are you different from your competitors?

You could list the functions and features you think set you apart. Rest assured, your competitor will have the same bullets in her next sales presentation.

You could tell them that our data sets are more comprehensive and that our analytics based on better science. The customer will nod politely and glaze a bit.

You could tell the client how we work differently, how we really listen and respect them and want to be their trusted advisors. But talk is cheap and easy to copy.

Or, if the question comes after a conversation (or two) in which you’ve been curious and empathetic; if you’ve shown up reliably, humbly and generously; if you’ve asked questions that helped them get to deeper understanding of their puzzle and fresh insight; you might simply ask them: “What would you say? What difference have you seen?”

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Talk Like Cave Man

When executives complain about a manager’s wordiness or failure to get to the point in meetings, they might say, “He thinks out loud.”
When a business leader hears you say something succinctly, she believes you’ve said it before, that you’ve thought it through and probably tested it already in conversation with others.

Thinking out loud, or verbal drafting, is essential preparation for any business meeting or presentation.

School prepares us to write out our ideas, to make outlines, to develop thoughts using external media like paper and pens and index cards and now screens and keyboards.  In an interesting paper, philosopher Jonathan Gilmore suggests that the incentives, constraints and risks involved in verbalizing thoughts in public are so immediate and urgent that they lead to systematically different “products.”  Or, as one coach puts it, we speak with a different part of the brain than we write with.

In my workshop on presenting proposals to executives, we do an exercise called “Cave Man.”  Here are the rules:

Using a total of twenty words or less answer aloud all of the following questions:

  • What is the executives’ starting point for this discussion?
  • What do you know that they don’t know?
  • What exactly are you proposing?
  • How will this benefit the business?

Speak telegraphically.  Use words as tags.  Gesture freely. Trust us to connect the dots.

“Cave Man” might sound like this —

E-mail marketing broken. 1% response bad. Piloted new messages, customers’ own words. 7% response! Expand! $2m new revenue.

— the sort of telegraphic speech that evokes Tarzan or the cave man of 1960s movies or modern-day insurance commercials.

“Cave Man” gives people the experience that Gilmore writes about.  They discover when they commit to a word or phrase, it comes out.  Sometimes what comes out is surprisingly clear and direct, maybe something you didn’t know you knew.  They also see that their arguments are not really streams of words but discrete beads that can be arranged with precision.  They become more articulate.

Thinking aloud is a great way to think. It’s just that you need to do your thinking before the meeting.

Verbal drafting surfaces fresh ideas, polishes them into economical expression and helps you internalize them so they’re at hand when you need them.

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Empathy as Inspiration

I sit across the table from an anxious exec in a windowless room.

“I’ve got this guy on my team, critical to a project that can’t fail. He can’t quit,” he said. “Problem is, we can’t give him the promotion he wants. He’s not really ‘promotable’ — and his review is tomorrow.”
“How can I help?”
“I need some graceful way to, well…”
“String him along?”
“Sort of.”

I turn on the video camera.

“Let’s try it. I’ll be him. What are you going to say?”
He starts. “It’s too early to tell what’s going to happen with promotions. You know it’s a crap shoot. We should talk again in a couple of months. I’ll have a clearer sense of…” And so on.

I turn off the camera. I show him the playback.

“Oh my God. I’m lying. Look at my eyes. Look at my hands. How do we fix that?”
“We can’t fix that. If you’re lying, he’ll know.”

We sit quietly. Things sink in. Then I ask: “If the roles were reversed, if you were the indispensable, non-promotable guy, what would you want him to tell you?”

He thinks for a minute. I turn on the camera.

“You’re critical to this project. It won’t succeed without you. You’re the only person on the team, maybe in the firm, with the skill and expertise to make it happen, and you know how important it is. I want you to know how much…” He is clear and direct. Suddenly he stops. “Turn off the camera.”
“You want to see it?”
“I don’t need to. I just got an idea.”
“I just figured out how to change his job, how to make it more interesting and set up a role he can shine in.”
“Where’d that come from?”
“I don’t know. It just hit me.”



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Find a Bug

I saw a small boy, maybe five or six, squatting on the sidewalk in front of the grocery store, staring intently at something. An old man with stringy gray hair limped up and squatted down beside him. I could hear only the old man’s side of the conversation.

“Cool bug… What do you think it is?… How about them horns?… Look how he walks… Huh, well….”

The boy was completely engrossed in the conversation. Both were completely engrossed in the bug.

Finally the old man stood up and said, “See you later,” and headed off.

Self-consciousness happens when we’re facing each other, when we’re trying to get something, fearful of failure or judgment. When we have something to look at together, something to play with, intimate connections happen organically. A bug magically turns strangers into friends.

People tell me that their best first dates, the ones where they really made a good connection and got to know someone new, were ones where something startling suddenly absorbed all the attention — a bug in the salad, a stickup, car trouble, torrential rain — and “gave us something to do together.”

When you meet with a prospective customer, you can try to dazzle them with your expertise. You’ll probably feel like you’re performing for a critical judge.

Or you can invite them to share their puzzle — “What are you trying to do? What seems to be happening? What have you tried? How do you want it to work? What difference would that make for your business?” — and give them one insight that might help them think differently about it.

Find a bug. They’ll forget it’s a sales call.


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Answer the Right Question

A mentor gave me this advice: “The customer doesn’t want you to solve his problem before you really understand it. The problem is an opportunity for conversation and connection, to have fun and build trust. Don’t solve the problem too quickly. Make a good conversation last as long as you can.”

If, like me, you like being an expert or need to feel useful (or be right), it’s tough to resist solving a problem as soon as you see one. We pounce on whatever smells solvable.

Curiosity is a reliable source of fresh inspiration for us reflexive fixers.
Wonder: What’s really going on? What is this puzzle really about? Why does she care so much?
If you practice curiosity, you can override the impulse to fix and learn to hear the “question behind the question.”

I overhead this conversation at my friends’ house:

SHE: Do these pants make me look fat?
HE: I love you so much it terrifies me, and every morning when I wake up beside you, I can’t believe how lucky I am — and I don’t much like those pants.

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