Lesson 5: Managing expectations means holding stakeholders to account early - before the horse has bolted

By Gary Gamp

For the fifth lesson in our 10 Lessons for 10 Years series, Sophie Pentony sat down with our CXO, Gary Gamp, to discuss why managing expectations isn't a corporate cliché - it's the foundation of accountability. Because once the horse has bolted, every conversation starts to sound like blame.

Bringing people on the journey

Sophie: Gary, talk me through what this lesson means to you, and where it comes from.

Gary: It goes back to why we started smart/tasking. Most organisations aren't good at managing expectations. When things go off track, people often hide the problem rather than address it.

Our ethos was to build a company that is completely outcome focused. To do that, you have to bring people with you on the journey. It’s difficult because it often requires delivering messages that clients don't necessarily want to hear.

I actually recorded an episode about this on our podcast, The Company Doctor, called Don't Make a Drama Out of a Crisis. The title was an old insurance company's strapline, but it became a mantra for us: whenever you find yourself in trouble, fix it without creating a massive drama around it.

Dealing in the truth

Sophie: How do you actually put that into practice? Is it just a willingness to hold yourselves accountable and be entirely honest?

Gary: Exactly. It’s based entirely on dealing in the truth, which sounds obvious but rarely happens in corporate life.

A classic example: You're running a project that’s due to land on Friday, but it's delayed. Many people would instinctively say, "We'll have it to you Monday" because they want to please the client in the moment. The problem is they often know that's unrealistic. Managing expectations means being honest: "It's more likely to be two weeks, but we'll do everything we can to improve that." I actually talked about this exact trap on The Company Doctor recently, in an episode about Managing Expectations Without Being a People Pleaser.

The second element is looking through the lens of your stakeholders to genuinely understand what they need out of the process, so you can act accordingly.

The 3.5-billion-dollar lesson

Sophie: Can you give me an example of a time where expectations weren't managed properly?

Gary: I was leading a $3.5 billion outsourcing project involving 3,000 people across 39 countries.

I built a transition team of 50 and arrived at the customer kickoff with 30 of them. The customer stopped me at the door and said, "You're not bringing them in here."

I hadn't managed their expectations ahead. I thought I was demonstrating strength; they saw it as overwhelming.  It was the right idea, executed the wrong way and I was deeply embarrassed sending people home.

Sophie: What do you do when you encounter a tricky stakeholder who intentionally ignores the loop, avoids risks, and reacts poorly when those risks become reality?

Gary: Sometimes, a customer doesn't want to manage expectations because it’s personally painful for them. I see this a lot on complex programs where a client tells me, "I can't tell my manager about this because it won't go well." Once you do that, you're trapped in a perpetual lie, which helps absolutely no one.

If someone isn't responding, document everything and lean heavily on governance and cadence. People don't want surprises. You need weekly or monthly sessions to flag those red flags while you still have the runway to fix them.

For example, on consulting projects, we rely on client data, but we know it’s hard to get. Rather than waiting three weeks and blaming the client, we flag the risk early: "We need this by next week. If we don't get it, it will create a problem." It might be uncomfortable, but it's far better than a surprise later.

Sophie: If someone is reading this and stepping into a leadership role, what is the very first conversation they need to have with their stakeholders on day one to set this up?

Gary: I always warn people against ‘watermelon reporting’ - green on the outside, red on the inside. If there's one lesson here, it's this: don't wait for a project to become a watermelon. Raise risks early, be honest about reality, and give people time to act.

Cleaning your house first

Sophie: So, it's about setting a clear expectation of transparency from the start.

Gary: Exactly. But the most critical rule for any manager is that you must clean your own house first. You have to stand on a steady foundation. If your own internal delivery isn't working, you won’t earn credibility.

10Strong takeaway

Don't let your project status become a watermelon - green on the outside but red on the inside. Proactive accountability means fixing your internal delivery mechanics first so that you earn the right to hold your external stakeholders to account early, long before a problem arises.