Real situations from real agencies.

Asking too many questions might be killing your sales potential.

A client had a prospect that wanted a small pilot. They got back a list of questions and a quote five times their budget (accounting for all the uncertainty).

I don’t blame anyone involved. The technical lead did exactly what had worked for them for 15 years. Before you price software, you need the full feature list. You need to understand the integrations, the compliance requirements, the edge cases. So they sent over a long list of discovery questions and priced for what they didn’t know.

That approach used to work. But I don’t think it does anymore.

Buyers right now want very little friction. A lot of them either don’t know the answers to those questions yet, or don’t want to spend time figuring them out before they’ve even decided to work with you. Every question you send is another reason to put the email aside for later.

What we suggested instead: make the decisions yourself, and show them what’s possible at different budget levels.

Here’s what you get at the low end. Here’s what you get in the middle. Here’s the full version, if and when you’re ready. With a unique technical plan for each.

You’re still doing the thinking. You’re just doing it for them, instead of handing it back as homework.

And most importantly, you’re not asking them to send 5 different people on their team Slack messages to get your questions answered. You’re giving them something to point to and say “We want that one.”

Show people what they can get. Don’t hand them a questionnaire.

Most of the sales calls you take are quietly deciding what you think you’re worth.

A client walked me through their pipeline recently. The large majority of their sales calls were with very price-sensitive buyers. Small budgets, lots of haggling, every dollar questioned.

That’s fine on its own. The problem was what it did to their head.

When a bigger buyer came along, one who’d picked them for their expertise and not their price, they quoted the same way. All those other calls had trained them to expect pushback, so they priced to avoid it.

We split every prospect into three buckets. People who were mostly shopping on price. People who wanted them specifically for something they were known for. And people who were looking for the best partner they could find, wherever that was.

Each bucket got its own pricing expectations. The third bucket, the most lucrative one, finally got priced like it.

On the very next call with one of those buyers, they raised their quote by 25 to 30 percent. The customer didn’t blink.

That’s the part that stuck with me. Nothing about their work changed between Monday and Tuesday. No new hires, no dramatic process change. The only thing that changed was what they believed their work was worth. 100% psychological shift.

If you’ve never had a client push back on your price, you don’t actually know where your ceiling is. You only know where your comfort zone is.

Keep raising your rates until you hit real resistance. Until then, your rates aren’t telling you much.

Someone on the client’s executive team kept overruling the team every week. The project was about to end... badly.

This was on a long-running retainer. A senior executive on the client side suddenly started showing up to the weekly meeting, looking at decisions the two teams had already worked through together, and overturning them. No context, no discussion. Just “let’s try a different way.”

The agency team was frustrated. So was the client’s own product team, who felt like they couldn’t stand behind anything they’d agreed to. The relationship was heading toward an ending nobody really wanted.

They thought about just firing the client, but I wanted to cut past the frustration and ask some valuable questions.

Do they like the work they’re doing? Yes. Do they like the team they work with? Yes. Does the executive seem like a bad guy? No. Suddenly, this all seemed salvageable.

So instead, the founder ran a full retro with everyone in the room: the executive, the client’s product team, and the agency’s design team. Not a true retro, actually — the project was still under way. Call it a reset.

The most important thing was the order. They let every side speak first and put all the cards on the table. Only after everyone else had said their piece did the founder share their own view.

It changed the temperature of the room. People on the client side who’d been quietly frustrated for weeks—and going behind their own executive’s back—finally said so. And it turned out the executive didn’t have a problem with the work. They just didn’t understand how the decisions were being made, because they weren’t around for any of it.

As soon as that executive got a walk through the process, they were apologetic and even impressed.

The fix was almost boring. The executive joined the team’s channels and came to a couple of working sessions a month. They stopped arriving cold, and the feedback was instantly more constructive.

The project got extended instead of ending.

When projects are mid-flight, it can seem like nothing can change the course. But sometimes, you need to slam your foot on the brakes and wrestle a stray project back on track.

When you click send on your invoices, do you say a little prayer that it’s not the last time?

A client had a pattern with their retainers. Six-month terms, and a lot of clients leaving right at the six-month mark. It always felt sudden. Everything seemed fine, and then an email would arrive saying they’d decided to go a different direction.

Here’s what I think is actually happening in most of those cases.

Somewhere around month five, the client has a conversation internally. Is this worth it? Are we getting what we expected? Should we keep going? And that conversation happens without you in the room.

By the time you hear about it, the decision is already made.

So my advice was simple: start that conversation yourself, about a month before the term ends. Do it openly. Something like, “We’re coming up on six months. I want to talk honestly about how this has gone, and what the next six could look like.”

A few good things happen when you do this.

You take the decision back into your own hands. You’re part of the discussion instead of waiting for a verdict.

You hear the concerns while you can still do something about them.

And if they are going to leave, you find out weeks early instead of the week of. That gives you time to fill the gap instead of scrambling.

It also saves you from the thing most of us have done at some point, which is sending next month’s invoice and nervously hoping it gets paid.

Agencies thrive on predictability, and clients thrive on knowing their agency is one step ahead of them. This is a great way to achieve both.

They listed all the extra work they’d done. The client called within the hour, and not to say thanks.

Here’s how it happened. A client was several months into a big project when they realized they were roughly 40% over budget. The work had grown. They’d said yes to things along the way, the way you do when you want the client to be happy.

So they wrote it all up. Here’s everything we did beyond the original scope, and here’s what it cost.

The client’s response was immediate, and it wasn’t about the list. It was about everything else. Quality. Rework. The team being slow. Not enough project management.

I’ve seen this play out a lot. When you ask for money after the fact, the client doesn’t hear “we did extra work.” They hear “we’re surprising you with a bill.” And once they feel surprised, every frustration they’ve had on the project comes out at once.

Three things would have changed the outcome.

One, flag it before it happens. The moment you see the scope growing, say so, while the client can still make a choice.

Two, make extra work a decision. “We’d love to go further on this, here’s what it would take” is a completely different conversation from “we already went further and now we’re here to collect.”

And finally, my favourite. Build in some room up front for extra work along the way. I like a small discretionary fund, maybe 10% of the budget, that’s approved at the start and only used if it’s needed. It’s easy for the client to approve because technically it’s already in the budget.

None of this is complicated. It’s mostly timing.

“We went over and here’s a surprise bill” is a negative confrontation 100% of the time. But showing you’ve prepared for overages and slight deviations on the plan? That’s a great way to look like experts.

A client cancels this week’s work. What does your team do on Monday?

A client of mine hit a slow stretch recently. Part of it was intentional, because they’d turned down work that wasn’t a fit. Part of it was just summer. Either way, people had nothing on their plate, and the founder wasn’t sure what to do with them. He was worried, because downtime is too easily interpreted by the team as a distressed company.

This is one of those problems that’s much easier to solve before it happens.

What I suggested: ask everyone to bring their own downtime project to the table ahead of time. Not something you assign. Something they choose.

The question is basically this. If you had a free day every week, what would you work on? Ideally it’s something connected to the company, like case studies, an internal tool, or a talk they’d love to give. But it can also be pure skills development.

At a brand studio I worked at years ago, one designer was fantastic at type design. Whenever they had downtime, they worked on a custom typeface we could sell. Nobody had to think about it. The project was just there, waiting.

That way, when a client suddenly pauses, the message isn’t “sorry, nothing for you this week.” It’s “good news, go work on your thing.”

One caution. If downtime is a gap between projects, it doesn’t really matter how much there is, as long as work is coming. But if more than about 20% of your team’s billable time is going to side projects, that’s not a gap anymore. That’s a pipeline problem.

Plan for downtime before it hits.

Ten wins. One slide each. Applause after every single one.

A client asked me how to get the whole team excited at their quarterly all-hands. They had an offsite planned, and they wanted people to leave feeling bought into where the company was going.

The way I’ve always done it is pretty simple. Lead with wins, and really lean into them.

I don’t mean one slide titled “Highlights.” I mean ten big wins: an exciting new client, a great piece of work, someone who went above and beyond, a key new hire. Give each one its own slide. Pause. Let people clap.

It sounds a little corny. It works.

The tricky part is the goals that didn’t go well. If you only talk about the ones on track, people notice what you skipped. But if you put the misses up there with someone’s name next to them, that person spends the rest of the meeting feeling awful in front of their peers.

So I frame misses as opportunities, and I make them the whole team’s problem. Something like: “We didn’t get as many leads this quarter as we wanted. Later today we’re doing a short workshop on it, and I want everyone’s ideas.”

That doesn’t mean nobody’s accountable. It just means accountability happens one on one, not on a stage.

It’s simple psychology, really. Encourage the behaviour you want to see, and find creative ways to correct the rest.

Celebrate in public. Hold people accountable in private.

A client showed me a proposal they were about to send. Honestly, it was great. Clear, well designed, strong case studies.

The fixed price looked good too... until, just out of curiosity, I said, “So, tell me about the project.”

They’d had several scoping calls with this prospect, and nobody on either side could clearly say what the project was. One of the prospect’s own people described it as “a website with five tabs.” It was very obviously not a website with five tabs.

When the scope is that fuzzy, a fixed price is a trap. Either you pad it so much the client balks, or you price what you think they mean and spend the next six months finding out what they actually meant, on your own dime.

So we called an audible and changed what the meeting was for. It became an alignment check, not a pricing conversation. Walk through the proposal together. Is this what you’re picturing? What’s missing? What’s in here that you don’t need?

Then, have two paths ready.

If they confirm the scope, great. Here’s your fixed price.

If there’s still real uncertainty, offer a retainer for a dedicated team instead. They pay for capacity each month, and you figure it out together as the picture gets clearer.

Some people worry this adds friction to the sale. It does, a little. I think that’s healthy. A small amount of friction before the price protects both sides from a much bigger amount of friction later.

We love to obsess over fixed pricing. But you can’t fixed cost your way out of a bad project.

Their company page had about 400 followers. The founder had more than ten times that.

A client asked me to help with a marketing plan. In their heads, that meant a content calendar for the company page. A few posts a week, maybe some ads. The usual.

But when we looked at what was actually working, the picture was different.

Every time the founder reposted something the company had made, it got real engagement. Comments from people he knew, shares, the occasional message from someone who’d been meaning to reach out.

There was an even better example. The team had built a small community tool on the side. On social, it got a modest response. Then the founder started bringing it up in meetings with people in his network, and it took off. It opened doors a post on the company page never would have.

So we flipped the plan. Instead of a generic social strategy, build around what was already working: the founder’s network and the company’s reputation for really good work.

That meant the founder posting more, with the team helping him do it. It meant giving him things worth talking about. And it meant being okay with the company page playing a supporting role.

I see this at agencies all the time. People trust people, especially early on. A logo doesn’t have relationships. You do.

Build your marketing around what’s already working for you, even if it doesn’t look like what a marketing plan is supposed to look like.

“We’ll build you a website.”

That was pretty much the whole scope in a client’s contracts. And their projects kept going over budget.

When the team looked into it, their first conclusion was: “Well, we need to budget more.”

Maybe (probably... usually). But I think the bigger issue was that nobody, not the client and not the team, knew where the project was going or when it ended.

If the contract says “a website,” you’ll keep building until the client stops asking. And if you try to challenge them before they decide the project is done, you won’t have a good reason.

The fix we landed on was one extra checkpoint. Not a new contract, and not a big process change.

After discovery, before wireframes, the client signs a detailed scope. Not “a website,” but “these 12 pages, on this platform, with these features, with this many rounds of revisions.”

My client made a good point: clients will push back, because they don’t want to be locked in. The honest answer for their client: a clear scope is how we deliver on time and on budget. It protects both sides. We’re not saying things won’t change, but we need a plan today.

And it does a few other useful things:

• It boxes in your team’s time, not just the client’s expectations.
• It lets you build a real schedule, with dates you can stand behind.
• When something changes, there’s a signed document to point to, instead of a he-said, she-said.

My favorite position to be in on a project is one where, if there’s a delay, everyone can see exactly why. That’s what this gets you.

Sometimes, it’s one quick checkpoint that makes all the difference, and heads off a lot of difficult conversations later.

A client gave me three problems to fix:

1. Clients were leaving too fast.
2. Almost nobody was upselling.
3. Their account leads never thought strategically.

They’d been treating them as three separate projects. Better onboarding to stop clients from leaving. Sales training for upsells. Some kind of strategy workshop.

But when we looked closer, they were the same problem.

I was shocked to find that account leads were expected to handle a minimum of 8 concurrent projects. When you’re juggling that many, you’re just trying to get this week’s work out the door. There’s no time to step back and ask where this client should be in six months, or what else they might need.

No room to think means no strategy. No strategy means no upsells. Every week is you straining to keep your head above water. And clients who don’t see you thinking ahead start wondering what they’re paying for.

So the fix wasn’t three initiatives. It was:

• Fewer accounts per lead.
• A clear mandate: think about where this client is headed, not just this month’s deliverables.
• Making sure every lead knows what’s upsellable. It sounds obvious, but often they don’t.
• A share of what they upsell, so growing an account pays off for them too.

When a team keeps missing opportunities, it’s tempting to blame skill or effort.

Check their workload first.

“Are we working to hit a high standard, or are we working to get his approval?”

Someone on a client’s team asked me that, and I haven’t stopped thinking about it.

I’ve seen this pattern at a lot of agencies. The founder drops into a project, asks for changes, and the result is... almost the same thing. Just done their way.

Nobody means harm by it. Founders usually got where they are by caring a lot about the work. But from the team’s side, it looks like this: you make a call, it gets changed. You make the next call, it gets changed. Eventually, you stop being opinionated and start guessing what the boss wants... instead of what the client wants.

One person put it perfectly: “I’m paid to be creative, but in practice I’m doubting myself the whole time.”

The question I give founders now is simple. Before you step in, ask: is this the company’s standard, or is it just my way?

If it’s the company’s way, great. Write it down. Make it a standard everyone can see, so the next person doesn’t need you to tell them.

If it’s just your way, let it go. You pay a lot of people to make these decisions so you don’t have to. Plus, the outcome probably isn’t worse. It’s just different from how you’d do it personally.

And here’s the bigger fix: if you’re a founder working at the right level, it should be almost impossible for you to micromanage. You should be far enough from the work that you don’t even get the chance.

A client had a VP of sales who cost them nothing.

I mean literally nothing. No salary. He was 100% commission. An early friend of the founder who’d helped get the company off the ground.

On paper, a great deal. But it was one of the most expensive roles in the company.

Here’s what I heard when I interviewed the team:

• He didn’t track his dealflow or any numbers, so nobody knew what was working.
• He was still running the outreach playbook from years ago, when it worked.
• Feedback didn’t land. He got defensive, and he was a friend, which made it harder.
• As a result of all of this, the founder and COO kept getting pulled back into sales.

The founder’s plan was to become a pro partnerships person themselves, so they could coach their friend into the role.

I pushed back on that. At this stage of a company, your sales leader should be teaching you sales, not the other way around.

You need someone who shows up with a playbook, measures everything, and brings in new tactics before the old ones stop working.

That doesn’t mean the friend has to go. He was well liked and great for the culture. But he couldn’t run the department anymore. The options were either an honest conversation about his role and a reset on expectations, or bringing in an experienced rep to lead.

These are some of the hardest decisions founders make, because every company has people who helped build the company but aren’t an ideal fit anymore.

But as your company changes, the people often need to change, too. Sometimes they’ll change proactively, sometimes willingly, or sometimes not at all.

But the longer we prolong that reality that things have to change, the more it hurts us.

A client had worked with one of the biggest companies in the world for seven years.

About one project a year. Great relationship. Great work. And in seven years, they’d never asked for more. Every project was the client showing up and blessing them with another year-making revenue infusion.

When I asked why they never asked for more, the answer was something like: “If they wanted us to work on more, they’d ask us.”

That’s almost never how it works.

Clients assume you’re busy. They see your other work, they know you’re in demand, and they don’t want to impose. Unless you tell them otherwise, they assume you’re maxed out.

So it becomes a strange game. The agency needs work but doesn’t want to bother the client, and client doesn’t want to overload the busy agency. Both sides are making an assumption and nobody wants to make the first move. It’s a high school dance.

So the plan was almost embarrassingly simple: tell them. “We’ve grown, we have more capacity, and we’d love to do more with you.”

That’s it. No campaign, no pitch deck.

I learned this earlier in my career. Way back when I was at Metalab, a single enterprise client started with one small project, then asked for a couple of developers, then a few more. Eventually that one account covered a huge share of our costs. The work we were publicly known for was a fraction of our revenue.

The other thing to remember: what’s a huge project for you is a rounding error for a company that size. You aren’t asking for a big favour. You’re offering to solve problems they already have.

The easiest new business you’ll ever win is from a client who already likes working with you.

You just have to ask.

A client was told the budget. They came in under it... and they lost anyway.

Not by a little. The winning bids were less than half of theirs.

When they told me, I could hear the conclusion forming: “We’re too expensive. We need to drop our prices across the board.”

I get it. Losing a big deal that you thought was in the bag seriously sucks, and the easiest lesson to draw is the most painful one.

But I’ve been on the other side of this. Years ago, I lost a project I really wanted. We came in right at budget and got turned down flat. Months later I ran into the agency that won it at a conference. They told me, a little sheepishly, that they’d lost a ton of money on it. They just wanted the case study that badly.

You can’t compete with someone who’s willing to lose money to win. And you shouldn’t rebuild your pricing around them.

A few things are always true:

1. Enterprise budgets get spent. If the money’s approved, someone is getting it. Pricing yourself into the floor doesn’t make the budget smaller. It just makes your share smaller.
2. One weird outcome is one data point. Learn from it, but don’t let it become your strategy.
3. Ask yourself: if they’d come back and offered you the work at half your price, would you have wanted it?

Usually the answer is no, which tells you the price wasn’t the problem.

Lost deals teach you plenty. Just make sure you’re learning the right lesson.

PS. That agency who beat us out? They went out of business a couple years later.

A founder asked me which parts of their backstory to cut from sales calls.

They felt like they were rambling: too much about how they got started, how they learned design, big company milestones, etc.

My answer: don’t cut any of it. Make it longer.

People LOVE hearing how you got here. It’s one of the most human parts of a sales conversation, and honestly, it’s usually the most entertaining. I’ve worked hard on my own version over the years, and it’s often what people remember most from a first call with me.

But here’s the bigger point: turn it around.

On first calls, I ask the other person for their story. Not about the project yet. Just: “So how did you end up where you are?”

People are almost always caught off guard. Then they spend five minutes telling you about themselves, and the whole call changes. It’s warmer and more relaxed, and you learn things a list of discovery questions would never turn up.

You still cover the project. You still ask about budget and timeline. But you’re doing it as two real human people who’ve actually met, instead of a vendor and a buyer working through a checklist.

If you’re not getting to know each other as people on that first call, what’s the point of having it?