The Subtle Art Of Delegating Work

If you’ve ever found it difficult to get the results you want from other people, try out this simple management technique.

Like most of the founders I meet, when I started my first business, I was new to managing people. I loved getting s*** done and getting my hands dirty — so the idea of delegating work to others was unnatural. I’d rather do it myself!

When I did delegate, it often left me feeling frustrated. After delegating some task, I’d find out later that it didn’t turn out as I was expecting or wasn’t even close completion. I took it personally and it weighed on my mind. It felt like if I wanted something done right, I had to do it myself. As my workload increased, I was fast approaching burnout.

Be careful what you ask for

A few years ago, I was hiring a marketing manager. I asked our office manager to research out the relevant recruitment agencies, get in touch with each of them, and report back to me in a few days.

A few days later, the manager came back to me. They’d emailed several agencies — but most of them never responded. My heart sank… this didn’t help me one bit. “Did you follow up with a phone call?” I asked. The response came back that there were too many other priorities competing for limited time.

I reflected on this with a more experienced mentor. The manager had done what I told them to do. Yet, here I was — frustrated, knowing that somehow the way I delegated wasn’t working out for me. Then my mentor gave me some wise advice:

Delegate problems, not tasks

I realised that the problem of filling my calendar with qualified candidates hadn’t been explicitly delegated. If that problem had been solved, I could get on with interviewing and hiring the right person for the job.

Step 1: Delegate problems, not tasks

The idea of delegating problems instantly resonated with me. When you’re deep in execution mode, you naturally think in terms of critical tasks. Good delegation requires you to think in terms of end-states.

Once you identify the core problem to delegate — check that it actually solves your problem. For example, getting candidates in throughout the following week would have given me a scheduling problem. What I really wanted was to set aside a morning for interviews.

However, delegating problems is only the first step. The next part is even more important — to help them find their solution.

Step 2: Coach, don’t instruct

The job of a coach is to help others work through their problems and find their own solutions. When I started coaching founders, I learned some great techniques that I wish I’d known earlier in my career as a people manager.

The simplest and most relevant one to share is called the GROW framework, invented by Sir John Whitmore. Here’s how to use the GROW model when delegating problems:

1. (G)OAL: Establish the goal.

Once you’ve delegated the problem, ask your employee to explain what a good result would look and feel like. Answer any questions they ask to understand what outcome would resolve the problem. Once the goal is clear, make sure they write it down.

2. (R)EALITY: Examine the current reality.

Before jumping into solutions, allow the employee to build awareness of the situation. Use the following questions to stimulate reflection. Where are we now in relation to the goal? What’s working and what isn’t working? Is anything stopping you from making progress?

3. (O)PTIONS: Explore the options.

Next, you want to help your employee examine different options that could address the problem. Pose questions like: what are your options? What else could you do? Who do you know who has encountered a similar situation? Like any brainstorm, don’t shoot down options just yet.

4. (W)ILL: Establish the will.

Finally, get commitment and help them map out their next steps. Again, let them come up with solutions by asking questions like: what do you think you need to do right now? How will you know when you have done it? What resources can help you?

Scaling your business requires effective delegation

The need to adopt a coaching relationship with your direct reports intensifies as you grow your business. The best people love to solve problems — and they hate being micromanaged. This is especially true if you are hiring people better than you.

It’s also great for keeping your employees motivated. Solving problems helps people connect with their purpose, continuously learn new things, and stay in control of their own destiny.


If you liked this piece, please tap the 👏 a few times so other people can see it too.


About Dave Bailey:
I coach CEOs of funded, early-stage tech companies to help them reach Series A. I’m a Venture Partner at
Downing Ventures in London, Mentor at Google Launchpad and a serial startup founder. Previously, I built and sold tech businesses in the UK, US and Brazil. I studied at Oxford University, Stanford Graduate School of Business and Singularity University. For more info, check out Dave-Bailey.com.

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.