Team leader: tips to delegate work based on personal strength

There is a quote from Marcus Buckingham that has stuck with me for years: "Average managers play checkers, while great managers play chess." In checkers, all the pieces move the same way. In chess, each piece is unique — a bishop moves differently from a knight, and a good player knows how to combine those unique abilities to win.

I think about this a lot when it comes to delegation. Early in my management career in Singapore, I used to delegate by workload — whoever seemed least busy got the next task. It was fair on the surface, but it was lazy management. I was playing checkers. One of my team members was brilliant at data analysis but hated client presentations. Another was an incredible storyteller but would freeze up in Excel. By assigning tasks based on availability rather than ability, I was setting both of them up for mediocre output. It took me a while to figure this out, and I feel a bit embarrassed about it in hindsight :P

What delegation actually means

Delegation is not about offloading the work you do not want to do (though I have to admit, early in my career, it sometimes felt that way). It is about assigning the right work, at the right complexity level, to the right person — and giving them enough context to understand why it matters.

A few things I have learned the hard way:

Context matters enormously. Do not just hand someone a task and walk away. Explain why it needs to be done, how it connects to the bigger picture, and what "good" looks like. When I was junior, the managers who gave me context made me feel like a partner. The ones who just dumped tasks on my desk made me feel like a pair of hands.

You are still accountable. This is the part that surprised me when I first became a manager. The work your team produces has your name on it, even if you did not do it yourself. So double-check before it goes out to another department, to clients, to leadership. When something is not up to standard, you can either fix it yourself or work with the team member to fix it — time pressure usually determines which path you take.

If you cannot delegate effectively, you become the bottleneck. I have been here. You know the symptoms: you are busy all the time, nothing moves when you are on leave, you dread taking a day off because you know things will pile up. That is not a sign that your team is weak. It is usually a sign that you have not delegated enough — or not delegated well. T.T

Delegation is also how you advance. I think this is under-discussed. The way to get promoted to the next level is to have someone on your team who can do the work you are doing now. If you hoard all the interesting work, you make yourself irreplaceable in your current role, which sounds good but actually traps you there.

Understanding what each person can handle

The key to good delegation is knowing your people. Not just their job titles or resumes, but how they actually work. Some things I pay attention to:

Readiness and willingness. If someone shows both the capability and the desire to take on more, start gradually increasing complexity. Do not throw them into the deep end — unless they explicitly ask for it and you trust their judgment.

Hands-on vs. hands-off. This one tripped me up for years. I assumed everyone wanted autonomy. Turns out, some people want you to walk them through each step, especially when they are learning something new. Others prefer to read the directions and explore on their own. Andrew Grove made this point well in "High Output Management" — the degree to which you should be hands-on or hands-off depends on how mature the team member is in that specific task.

Adjust by seniority, but not rigidly. For fresh graduates, I am more descriptive — showing them how to pull a report with cost and revenue broken down by country for the last quarter, for example. For senior team members, it is more about aligning on the outline and key message, then letting them handle the execution. But even senior people need review. I always make time to check the final narrative to ensure it tells a coherent story.

Do not delegate without guidance. Especially if your team members are new to a task. "Figure it out" is not a delegation strategy. It is abandonment.

Think about growth, not just output. I believe anyone can learn anything given the right guidance — and every task is an opportunity for someone to develop. If you are delegating a presentation, think about whether this team member could use it to build their public speaking skills. If it is a client report, maybe it is a chance to practice executive storytelling. Ask your team members what they are interested in long-term — sometimes that conversation sparks an idea for a project that aligns with both their aspirations and the team's needs.

Keeping it fair

This part matters more than most managers realize. If your team feels like delegation is unfair — like some people are overworked while others coast — trust erodes fast. I have heard team members say things like "my manager does nothing and asks me to do everything" or "my manager takes credit for my work." Both of those are delegation failures, and they are more common than you might think.

Here is what I try to do:

Be transparent about workload. Everyone should know, at least roughly, what everyone else is working on and why. If one person is carrying a heavier load because they are the right fit for a critical project, acknowledge it. A simple "I know you have been doing more than your share this month, and I appreciate it" goes a long way. Extra time off, recognition in a team meeting, or a bonus if the budget allows — these all help.

Check in regularly. Schedule one-on-ones or group discussions about workload. If someone feels overwhelmed, redistribute where you can. (I wrote more about this in my capacity planning tips.) But also do not forget to praise the people carrying more weight — they need to know it is seen and valued.

Give ownership, not just tasks. There is a meaningful difference between "do this thing" and "you own this thing." The latter creates engagement. Ask for their input on the approach. Let them make decisions within their scope. The more agency people feel, the more invested they become.

What is your approach to delegation? I am still refining mine after all these years — I would love to hear what works for you.

Cheers,

Chandler