A founder I work with recently went away for a week on holiday. It was their first break for nearly a year and they would be in a different time zone with proper distance from the agency. They left clear instructions for the team before leaving. They’d explicitly set up what needed to happen: quarterly business reviews organised, renewal conversations handled, the usual account management basics were reiterated.
It was actually a good time for the founder to go away – clients were generally pretty happy and there weren’t many fires to be put out. Even the renewal conversations were expected to go well and didn’t seem too challenging. The team also weren’t stretched in terms of capacity and were in a good place.
So, what went wrong?
Well, the founder didn’t exactly get a peaceful week away. Their Slack and emails blew up more than useful with messages from the team asking questions that they should have known the answers to themselves.
Not just that, but when they returned to the office, lots of the projects that should have been well underway or completed had stalled.
Everything was delayed until the founder returned.
Here’s what made this revealing: the systems were already there. The team knew what needed doing. They had the capacity to do it. But they didn’t do it until the founder came back and could validate it.
This isn’t a story about poor planning or unclear responsibilities. It’s about something deeper: the team fundamentally doesn’t trust that work counts until the founder has seen it.
I’m going to share what we reviewed together when trying to unpick this issue and prevent it from happening again.
It wasn’t a systems or capability problem
When founders say “my team needs better systems,” often the systems exist. The team just doesn’t believe the work that comes from these systems is real until the founder validates it.
The founder in this situation had been explicit. They’d set clear expectations about what needed to happen while they were away. The team wasn’t confused about priorities or lacking authority to act.
But authority on paper doesn’t mean authority in practice.
What actually happened is that the team treated the founder’s absence as a pause button. Not because they couldn’t do the work or because they wanted an easy week. Instead, they’d learned, over time, that work doesn’t stick until the founder confirms it’s good enough.
The founder had accidentally trained their team into this way of thinking.
Think about what this reveals. If your team can’t complete their tasks when you’re away, they’re not struggling with capability. They’re waiting for your presence to make it “official.”
What “checking in” actually means
Teams reach out during your holiday for a reason. But it’s usually not because they need your answer to a question.
It’s because they need permission to believe their own answer is good enough.
This shows up in small ways at first:
- A message asking if they should send a particular email to a client.
- A quick question about whether a piece of creative work is ready.
- A check-in about whether now is the right time to have a renewal conversation.
On the surface, these look like reasonable requests for input. But underneath, there’s a pattern: the team has developed a habit where your approval becomes the final validation step.
Not because they lack the authority to make the decision – founders usually give them this. But because they’ve learned that decisions don’t become real until you’ve confirmed them.
When this becomes the norm, being away doesn’t mean that things carry on as normal and things get done. It just delays everything until you return. The work sits in a queue, waiting for you to make it count.
This even happens outside of holidays because the seeds are sewn way before that.
I saw this pattern recently where even straightforward client communication was being escalated. The team kept bringing things to the founder that they were perfectly capable of handling themselves. Not complex strategic decisions, just standard account management tasks.
The issue wasn’t that the team didn’t know what to do. It was that they didn’t trust that their version was the final version.
How you can accidentally train this behaviour
This behaviour doesn’t come from nowhere. Founders (and senior leaders) inadvertently reinforce it.
Every time you step in when something looks slightly wrong, even when the team technically handles it, you’re teaching them their judgment isn’t enough.
Every time you redo work or “just quickly fix” something because it’s faster than waiting for them to get it right, you’re showing them their version is never the final version.
The long-term cost of this is enormous. Your team learns that their work is always provisional. That the real work happens when you review it. That their decisions are suggestions until you confirm them.
I’ve seen this play out in agencies where the founder is constantly the escalation point.
- Client unhappy with a creative idea? Escalate to the founder.
- Account manager unsure whether to push back on a brief? Escalate to the founder.
- Team members can’t get the client to engage? Escalate to the founder.
At one agency, the founder was being pulled into client calls to explain the strategic rationale behind work because the account manager couldn’t articulate it in a way that satisfied the client. This wasn’t a one-off. It was the pattern.
The problem isn’t that the account manager lacks the information. It’s that the client has learned the founder’s explanation is the one that counts. And the account manager has learned they’re not expected to be the authority.
Every time you handle it yourself because it’s quicker, you’re teaching your team that their judgment doesn’t count.
I know – this is exactly what I did when I was running my own agency. I saw the cost and over time, it took its toll on me because all problems came via me.
The real cost isn’t you not being able to take your holiday
The real cost is that your agency has a ceiling that you’ll struggle to break through.
This pattern doesn’t just affect your ability to take time off. It fundamentally limits how big you can grow.
You can’t scale past a certain size when every decision needs founder validation. You hit a bottleneck exactly when the agency is trying to grow.
The cruel irony is that the harder you work to compensate for this, stepping in to keep things moving, the more dependent the team becomes on you.
The agency that requires your constant presence and will always be limited by your available hours. That’s not a team problem. It’s a structural ceiling.
And as I mentioned earlier, this can take its toll on you as a founder. You shoulder the load of client problems and become the default way to handle those problems.
It also prevents your team from progressing because they’re not learning to handle these issues themselves.
How to actually change this
Breaking this pattern requires practical shifts that start small but compound over time. This isn’t an overnight fix.
First, make explicit what “done” looks like. So that the team can self-validate.
If creative work is “done” when it meets three specific criteria, document those criteria. If a client conversation is ready to happen when certain conditions are met, write down what those conditions are. The team needs to be able to check their own work against a standard, not wait for you to confirm it meets an invisible bar.
This isn’t the same as setting up systems or processes to do work. It’s more about helping the team understand your expectations in a clear, tangible way so that they don’t need you to confirm them every time.
Second, deliberately create situations where you can’t be the validator, even when you’re available.
This is uncomfortable at first. You’ll watch work go out that isn’t quite how you’d do it. You’ll have to stop yourself from “quickly fixing” things before they reach the client.
But that discomfort is the only way out.
One approach that works: redesign one-to-ones to put the onus on the team member. Instead of you asking them what’s happening with their clients, require them to report on client performance and activities. They prepare. They present. They assess whether things are on track.
This forces autonomous accountability. They can’t passively wait for you to tell them what to do or whether their work is good enough.
Another shift: accept buffer time and imperfection in planning. If you’re trying to control every hour of every person’s time, you’re guaranteeing they’ll come to you for permission to deviate. Leave space for them to make judgment calls. Accept 90% accuracy rather than trying to plan everything perfectly.
The hardest part of this is letting go of the belief that your version is always better. Sometimes it is. But if your team never gets to own the final version, they’ll never develop the judgment to make it good enough without you.
This requires you to be uncomfortable. You’ll watch things happen that you would have done differently. You’ll resist the urge to step in. But that discomfort is the price of building a team that can function without you.
Get comfortable with being uncomfortable.
This is one of the hardest patterns to break because it feels faster and easier to just answer the question, approve the work, validate the decision.
In my experience, this works fine until you start growing past the 15-20 person mark. After this, it becomes unsustainable.
Every instinct tells you stepping in is helping.
But the long-term cost is an agency that can’t function without you. And that means you never get the space to actually lead it, let alone take a proper break.
The work starts with recognising the pattern isn’t about your team’s capability. It’s about what you’ve accidentally taught them counts as “real.”
Next time you’re away and your phone lights up with a “quick question,” ask yourself: are they asking because they don’t know the answer, or because they don’t trust their answer until you’ve confirmed it?