How to lose a client

And what to do when you do

I lost a client last week. I want to tell you about it while it is still fresh enough to hurt, because I think the hurt is where the usefulness lives, and if I wait until the sting has faded, I will rationalize the whole thing into a tidy lesson and miss what it actually has to teach me.

Here is what happened.

A client came to us with urgency. They needed two things: a technology build and a paid media campaign. They needed both immediately. They said two weeks. I said “Yes.” Just, “Yes.”

I should have said “Yes, But…”

Why I Said Just “Yes.”

I said “Yes” because Comma Eight is a service business, and service businesses have a certain reflex to say “Yes.” It’s muscle memory. Someone walks in with urgency and budget, and a problem they cannot solve alone, and you say yes, because saying yes is what you do, because you are helpful, because you are capable – because the revenue is sitting right there, which is not exclusively reserved for me, and all you have to do is reach out and close your hand around it.

Not only did we say yes… but we sacrificed normal onboarding for speed and for familiarity. This was, after all, a familiar client in a new role.

We did not have the time to understand their business with the level of specificity required by our work. We did not narrow the scope to something we could execute at the standard we hold ourselves to. We were, in the language I have been using in this newsletter, trying to keep it capital S, ‘Simple.’ Until, of course, Simple Stops Working.

Which it did. Nine days later, at seven o’clock in the morning, I received a text message. “Can you chat for two minutes?”

If you have been in the service business for any length of time, you know that a text message requesting two minutes of your time at seven in the morning is never two minutes and never good news. It is the professional equivalent of a girlfriend telling her boyfriend, “We need to talk,” which is itself the professional equivalent of hearing your full legal name called from another room by your mother.

He was ending the engagement.

The Twelve-Hour Gap

Here is the part that I cannot rationalize away.

The day before that text message, I had reached the same conclusion as the client. I was going to call him in the morning. But I was going to say something different. Something I believed (and still believe) would have been more helpful:

I was going to tell him that the scope was too wide, too fast. We do not understand their business well enough yet to spend the paid media budget wisely. I was going to suggest that they let us narrow to the technology piece, prove ourselves there, and earn the right to expand. Let us slow down so that the work we do is work we are proud of, rather than work we survived.

I did not make the call because the day ended, and I told myself I would do it first thing tomorrow. And tomorrow, at seven o’clock, the phone buzzed.

Twelve hours.

That is the gap between what happened and what should have happened.

The Ladder and the Fire

The metaphor I keep reaching for is imperfect, which is usually a sign that it is the right one, because clean metaphors tend to hide the mess.

A house is on fire. You build a ladder. You get the person out of the window. And then they fall, because the ladder was constructed in a panic by people who were trying to be fast when they should have been trying to be right. Did you rescue them? In a sense. But they also broke a bone on the way down, so the conversation afterward is never going to be about the fire you saved them from. It is about the leg they broke on your ladder.

Our problem is that we built a fast ladder.

We got the client through the window. But the descent was rough enough that the rescue won’t be what they remember.

The instinct, in a moment like this, is to say something like:

“We moved mountains. We did (good) work. We mobilized in forty-eight hours. We put our best people on it. We worked nights and on the weekends. The fire was real, and we showed up.”

All of that is true. But none of it matters. Because the client did not hire us to be heroic. They hired us to be competent. And competence begins before the first deliverable and in the conversation, where you negotiate what “yes” actually means.

The “Yes” and the “Yes, But” Organization

Are you a “yes” organization or a “yes-but” organization?

If you are having trouble answering that question, let me help you:

A yes organization takes the revenue, scope, and timeline as presented and says, “We will figure it out. We are smart, we work hard, and we have done harder things.”

Now, there is an energy to this that I find admirable and do not want to lose. It’s this willingness to jump that makes a small company competitive. Large companies have processes. Small companies have nerve.

But nerve without discipline is just recklessness that has not been caught yet.

A yes-but organization, on the other hand, takes the relationship but negotiates the terms.

“Yes, we will help, but not with everything at once.”

“Yes, we will build the technology, but the paid media waits until we know your business well enough to spend your money as if it were ours.”

“Yes, we will move fast, but fast includes a week of onboarding that we are not willing to skip, because the onboarding is the foundation and a foundation poured in a panic cracks under the weight of everything you build on top of it.”

I want to be the second kind of organization. But it’s hard. And the reason for this is that saying no to revenue in a service business is like saying no to dessert when it is already on the table, and everyone else has ordered the chocolate cake. The discipline exists in theory. In practice, you eat the cake.

So if you are not going to do it for yourself, at least do it for your team.

What I Owe the Team

My team worked hard on this.

They moved fast because I told them to, and they delivered because that is what they do. They produced work that, given the constraints, was impressive by any standard I know how to apply.

And now I have to stand in front of them and explain that the client is gone. And I have to find a way to communicate two things simultaneously that sound contradictory. I need to tell them that the work was good, the outcome was bad, that while they did their jobs, the engagement failed, and that both are true, and neither cancels the other.

Because my team did not fail. The scope failed. The onboarding failed.

The conversation at the outset, where someone should have said “here is what yes means and here is what it does not mean,” failed.

And these failures belong to me, and I want to be precise about that, because the temptation to distribute blame when the alternative is absorbing it is strong, and I do not intend to give in to it.

But I also want them to learn something from this that I am still learning myself.

And that is that while I was willing to say yes, they should not have been.

What to Actually Do

I have read enough business advice to last several lifetimes, and most of it is useless. The reason is that it is written by people who have already processed their failures into frameworks and drained them of the specific, painful, instructive details that make them worth learning from. So what I want to share with you is not a framework. It’s what I am actually doing, this week, in the aftermath, while it still stings.

1. I am writing down what happened. Not just the narrative, the sequence. What was said, by whom, on what day. What was promised? What was delivered? Where the gap between promise and delivery first appeared, and why I did not address it when I saw it. This is not going to be a pleasant task, but it will be incredibly useful for the next two things I plan to do.

2. I am going to have a conversation with my team that does not begin with “here’s what we’ll do differently next time.” It begins with “here’s what I should have done differently.” Because the instinct after a loss is to look forward, and looking forward is important, but not before you have looked at the specific thing that went wrong with enough honesty to actually see it.

3. I am going to listen and not challenge the client. I will not win the business back or argue. Because the client’s version of what happened is not the same as my version, and the truth is probably in the gap between them – I will not find it by telling my version louder.

4. I will then take all of this information and write, in a document that no one will see, the sentence I should have said on day one. For this client, the sentence will probably be something like: “We can absolutely help with the technology build. Paid media has to wait 30 days until we understand your business well enough to spend your money wisely. I know that’s not what you want to hear, and I’m telling you anyway.”

To Sum Things Up

If you struggle with saying no to revenue, you’ll end up with less of it.

Discipline is the only real growth lever in a service business.

To stop being a “yes organization,” give your team permission to push back:

• Hold the scope line.

• Don’t skip onboarding.

• Protect the team so they can do what they do best.

If someone asks, “Can you do this in two weeks?” say yes like this:

• Confirm what “yes” includes

• Confirm what “yes” excludes

• Lock the onboarding timeline first

• Then you can move fast without lying.

If it doesn’t work out, here’s the post-mortem checklist that actually teaches you:

• Write the sequence of what was said

• Identify the first promise/delivery gap

• Name the exact moment you could’ve corrected it

• Record the sentence you should’ve used day one

And when you lose the client, don’t argue your version louder. Do this instead:

• Call to listen

• Ask where their expectations diverged

• Seek the gap, not the blame

• The truth lives between narratives.

That way, the next time someone says, “Can you do this in two weeks?” I am going to pause, take a deep breath, and I am going to say, “Yes. But…”

Until next Wednesday,

Ashley Heron

Managing Director, Comma Eight