How Do We Know?

THE WONDERING | LEADERSHIP REVIEW

A leadership review of the evidence behind your most confident opportunities.

Gus Byleveld, The Wondering

Why this exists

When the revenue number becomes uncertain, most leadership teams do not suffer from a shortage of explanations. They suffer from having several.

Sales has a view. Marketing has a view. Customer Success has a view. Each describes something real. Each is defensible. And they do not agree with one another.

The difficulty is that the business does not pause while this gets worked out. It keeps investing in whatever produced the uncertain number. Opportunities age, capacity is consumed, spend continues against positioning nobody has tested, and the recovery requirement grows. A month of delay does not cost a month. It raises what the next quarter has to deliver.

This review exists to shorten that period, not by deciding faster, but by separating what the organization knows from what it believes.

Where this came from

Some years ago, I sold security technology to financial services institutions. Our prospects agreed the problem was real and agreed the technology worked. What they did not share was our sense of urgency.

The process moved forward anyway. Demonstrations, architecture reviews, technical teams, real time invested. Our pipeline looked healthy, and the engagement was genuine. That is not a weak signal. It is exactly the kind of evidence a leadership team treats as validation.

It went on for three quarters before we understood that the person who had to make the decision did not believe the problem was serious enough to act on. Every conversation was an education conversation. We were teaching a buyer why he should care, which felt like value and was, in fact, the clearest available signal that the problem was not yet his problem.

It ended because we missed our targets and ran out of time, not because anyone asked a better question. The answer, when it came, arrived by accident through a referral to the head of fraud, who carried a number that moved if the problem went unsolved.

That question was available to us from the first meeting. Nothing prevented us from asking it. What we did not have was anything in our process pointed at finding out who owned the pain.

This review is what we didn’t have.

What this is

A structured conversation your leadership team can hold in about ninety minutes.

It takes a small number of live opportunities and separates, question by question, what the customer has actually told you from what your organization has concluded. It produces one number: the proportion of your confident pipeline that rests on interpretation rather than evidence.

It is not a forecasting methodology, a qualification framework or a replacement for your sales process. It sits alongside them and asks a different question. Not where this deal is in our process, but what we actually know about the buyer’s decision.

What it is not

It is not a performance review. If you run it as one, the answers will be defensive, and the exercise will be worthless. More on that below.

How to run it

1. Bring the leadership team, not just Sales. Marketing, Customer Success,s and Product all hold evidence about the buyer that Sales does not, and the point is to assemble a picture no single function can see.
2. Choose three or four opportunities you feel confident about.

This is the instruction people most often reverse, so it is worth being explicit. Do not choose the deals that are already worrying you. Everyone knows those are uncertain. Interpretation hides inside the opportunities nobody is questioning, and those are the ones consuming capacity on the assumption that they will close.

3. Work through the five questions for each opportunity, one at a time, as a group.
4. Mark every answer. Not the quality of the answer, only its source.
5. Do not solve anything during the review. The instinct to fix a gap the moment it appears is strong, and it ends the diagnostic. Note it and move on.

The five questions

For each opportunity, answer each question, then mark it.

Evidence. The customer said or did this. It can be pointed to.

Interpretation. We concluded this. It is reasonable, and it came from us.

Unknown. We do not have an answer.

Notes on the questions

Why now is the one most often answered from the seller’s calendar rather than the buyer’s circumstances. Budget cycles and quarter ends are our timing, not theirs. Something has usually changed inside the buyer’s organization, and if nobody can say what, the urgency may be ours alone.

Who carries the cost is the question that would have saved me three quarters. A buyer can agree with your case and still never act, because agreeing costs them nothing. Somebody in that organization is measured on something this problem affects. If you cannot name that person, you are talking to an audience rather than a buyer.

What the buyer has done separates seller activity from buyer progress. Meetings, demonstrations, and proposals are things we did. Introducing us to a colleague, assigning internal resource, sharing an internal document, initiating a security or legal review, putting a date in their own plan: those are things they did.

Reading the result

Count the marks. Across three or four opportunities,s you will have fifteen or twenty answers.

There is no threshold and no score. The useful signal is simply the ratio, and where the interpretations cluster.

If most answers are evidence, your confidence is well founded, ed and the revenue problem is probably somewhere other than the pipeline you reviewed. That is a genuine finding and worth having.

If the interpretations concentrate in one question, that is more informative than a general count. Interpretation clustered on who carries the cost usually means the organization is talking to the wrong person. Clustered on why now, it usually means there is no real trigger, and the deal will move whenever the buyer feels like it. Clustered on what the buyer has done, the pipeline is measuring your effort rather than their intent.

Unknowns are not failures. An honest unknown is more useful than a confident interpretation, because it can be resolved.

Putting a cost on it

This is deliberately rough. It is an order of magnitude, not a forecast, and its only purpose is to tell you whether finding out is worth a week of effort.

Neither C nor E is precise, and neither should be presented as though it were. The question they answer is narrow: is this large enough to justify going and finding out?

In most reviews it is, by a considerable margin, which is the point.

What you cannot answer from inside the building

Some gaps close easily. If nobody knows what triggered the buyer’s interest, someone can ask on the next call. Some don’t close that way, and it is worth being honest about it.

If the review shows that your understanding of why buyers do or do not act rests mainly on interpretation, the evidence you need sits with people who did not buy—prospects who went quiet. Deals lost to no decision—customers who evaluated you seriously and chose something else.

That evidence is hard to reach for structural reasons, not effort. A buyer will rarely tell the salesperson who pursued them what actually happened, because the conversation is awkward and there is nothing in it for them. The salesperson cannot hear it neutrally either, since they were part of what is being described. And a chief executive making those calls personally doesn’t scale beyond a handful, and it changes what the other person is willing to say.

This is the single most common reason companies keep circling the same explanations. Not unwillingness, but the lack of a mechanism to hear from people who are no longer talking to them.

Whatever route you take to it, the principle holds. Explanations generated inside the building can be tested only outside it.

Running this without it becoming an inquisition

The design depends entirely on people answering honestly, which means the way it is run matters more than the questions themselves.

Mark answers, not people. Interpretation is not an error. Every commercial organization runs on interpretation, and it is often correct. The exercise establishes which conclusions have been tested, not who has been careless.

The most senior person should mark their own answer first, and should mark at least one as interpretation. Whether this exercise is safe is decided in the first two minutes, and it depends on what the chief executive does, not what they say.

Do not attach it to forecasts or compensation. The moment a mark carries consequences, everything becomes evidence, and the instrument stops working.

Resist solving. When a gap appears, the room will want to fix it immediately. Note it and continue.

Run it on a cadence rather than in a crisis. A review held only when the number is missed reads like an investigation. Held quarterly, it becomes a habit, and the comparison between quarters is more useful than any single result.

Why this works

Three bodies of research sit behind the design.

Treating conclusions as assumptions until tested. Rita Gunther McGrath and Ian MacMillan’s discovery-driven planning argues that when uncertainty is high, plans should begin by identifying what must be true for the plan to succeed, treating those items as hypotheses rather than facts and testing the most critical ones before committing further resources. Their observation is that conventional planning buries assumptions inside projections, where they are never examined. This review applies the same logic to an opportunity rather than a venture. Marking an answer as interpretation is simply naming an assumption so it can be tested.

Why the answers have to be safe to give, Amy Edmondson’s field study of fifty-one teams found that psychological safety, defined as a shared belief that the team is safe for interpersonal risk-taking, was associated with learning behavior, and that learning behavior in turn explained the link between safety and team performance. The practical implication here is direct. An organization cannot distinguish evidence from interpretation unless people can say, without cost, “We do not actually know.”

Why waiting is not the safe option. Barry Staw’s work on escalating commitment showed that decision makers responsible for a course of action tend to commit more resources after receiving negative results, rather than less. Continuing becomes easier to defend than stopping, and each additional commitment partly protects the ones before it. Applied commercially, an untested theory of the buyer does not sit still. The longer it goes unexamined, the more investment it attracts.

Two further findings inform the framing. McKinsey’s research on organizational decision-making found that most organizations behave as though speed and quality are a trade-off, while the data pointed the other way. And Matthew Dixon and Ted McKenna, analyzing more than two and a half million recorded sales conversations, found that between forty and sixty percent of deals are lost to no decision rather than to a competitor, with the majority of those losses involving customers who had already accepted the need to change and still could not act.

References

Dixon, M. and McKenna, T. The JOLT Effect: How High Performers Overcome Customer Indecision. Portfolio, 2022.

Edmondson, A. C. Psychological Safety and Learning Behavior in Work Teams. Administrative Science Quarterly, 44(2), 1999, pp. 350 to 383.

McGrath, R. G. and MacMillan, I. C. Discovery-Driven Planning. Harvard Business Review, 73(4), July to August 1995, pp. 44 to 54.

Aminov, I., De Smet, A., Jost, G. and Mendelsohn, D. Decision Making in the Age of Urgency. McKinsey & Company, April 2019.

Staw, B. M. Knee-Deep in the Big Muddy: A Study of Escalating Commitment to a Chosen Course of Action. Organizational Behavior and Human Performance, 16(1), 1976, pp. 27-44.

Gus Byleveld is the founder of The Wondering. He has spent more than twenty-five years in B2B technology in executive, chief revenue, and chief commercial roles. He works with chief executives of growth-stage technology companies to identify what’s holding back growth