Sales & new business

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.

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.

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.

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 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?