I was talking to someone recently about a creative agency that was struggling with their project management tools. The brief from management was basically: get our people to use Asana and Harvest properly.
And my first thought was, have you met your people?
Because the very qualities that make this agency brilliant are the same qualities that make those people resist filling in boxes. The creativity. The instinct. The beautiful chaos that produces the work their clients love.
That’s the value they bring to the table. - - - The imaginary team
Most systems are designed for a team that doesn’t exist.
The version of your people that reads the process document on day one and follows every step. The version that fills in every field, updates the board at the end of every day, and logs their time accurately without being asked.
That team has never existed. Not in any business I’ve ever worked with. And I’ve been doing this for a very long time.
What you’ve actually got is a mix of brilliant, messy, creative, distracted, talented humans who do incredible work in ways that don’t always fit inside a dropdown menu. Each business is different, you need a different type of people for a different type of output.
And if you build your system for the imaginary version, you’ll spend your life frustrated that the real version won’t use it. I did it at the beggining of that very long time I have been doing this. - - - The thing nobody says out loud
When you try to force creative, instinctive people into rigid systems, one of two things happens.
Either they comply. They start ticking the boxes, following the steps, filling in the fields. And slowly, without anyone noticing, you lose the thing that made them valuable in the first place. They become administrators who occasionally do creative work rather than creative people who happen to work inside a business. The output gets safer. The spark goes. The clients notice eventually, even if you don’t. This doesn’t really happen, well I have never seen it, but I would imagine this is how that story would end.
Or they resist. You label them difficult. You chase them. You send the passive aggressive Slack messages. You end up in a compliance battle that nobody wins. They’re frustrated, you’re frustrated, and the data still isn’t right because they’re filling things in to get you off their back, not because it means anything to them. Ahhhhhh.
Either way you’ve broken something.
The qualities that make someone brilliant at client work, at design, at strategy, at building relationships. Those are often the exact opposite of the qualities that make someone good at admin. You can’t have both in the same person. So stop trying. - - - Meet them where they are
This doesn’t mean letting people do whatever they want. I’m not saying throw out the systems and let chaos reign. You still need the data. You still need to know which projects are on track and which ones aren’t.
But you need to be honest about who you’ve got and design around that reality.
I worked with a creative agency recently where the founder told me on day one: no timesheets. Under no circumstances. Because she knows her people. She knows they won’t fill them in. And she knows that if she forces it, she’ll either get bad data or she’ll damage her culture. Probably both.
So we found another way to capture the information. The people who are good at scheduling and planning and numbers do that bit. The creative people do what they’re good at. We didn’t ask anyone to become a different person. We just worked out who was already good at what and built around that.
That’s what meeting people where they are actually looks like. Not lowering the bar. Not accepting poor performance. Just being realistic about which humans are going to do which bits and designing accordingly. - - - I used to get this wrong
I’ll be honest. I used to build systems for management reporting. I’d start with what data the founder or the leadership team needed to see at the end. Then I’d work backwards and design the system to capture it.
And they kept not working.
Not because the data was wrong. Not because the tools were wrong. Because I was designing for the person reading the report, not the person feeding the data. The system looked beautiful from the top. From the bottom it felt like admin for someone else’s benefit.
When I shifted to starting with the people who’d actually use the system, everything changed. What’s the minimum I need them to do? What’s the easiest way for them to do it? What can I automate or get someone else to handle so they don’t have to?
Most systems are designed to win the vote of the MD. If you ask the MD to pick, they pick the one with the most tick boxes. If you ask the creative person, they pick Notion and you get nothing useful out of it. (No offense to Notion it’s just really good at tracking creative stuff). The answer is neither. It’s a third thing. And you only find it when you’re honest about who’s actually going to use it. - - - The cost of fighting your culture
This matters more than most founders realise.
If you design a system that fights your culture, you don’t just get bad data. You signal to your best people that you don’t understand them. That you’d rather have compliance than creativity. That the way they work, the thing that got the business to where it is, isn’t good enough any more.
In a small business where those people are your competitive advantage, that’s an expensive signal to send.
The agency with the beautiful portfolio. The one winning awards. The one where clients stay for years. That exists because of who those people are. Not despite it. If you try to sand off the edges that make them difficult to manage, you sand off the edges that make them exceptional.
I’ve watched it happen. An owner gets frustrated, brings in a consultant, puts in a rigid system. The most talented people leave. The ones who stay become less interesting. The work gets flatter. And the owner can’t work out why revenue’s dropping when the systems are finally running smoothly.
The systems were running smoothly. The business wasn’t. Because the people who made it special were gone.
Start with who you’ve actually got. Be honest about what they will and won’t do. Build from there. Everything else follows. - - - If you’re stuck between wanting better systems and not wanting to break the culture that makes your business work, that’s exactly the tension I help people navigate. I run free 90 minute strategic sessions where we look at what’s really going on, who your people are, and what a system that actually fits would look like. No pitch, no obligation. Just a proper look under the bonnet. Drop me a message if you’d like to book one.