How to delegate more and focus on strategy

Dream Team
4 min readMar 30, 2021
pic by Hannah Busing — Unsplash

We talked about delegating in our From Freelancing to Agency article. But the issue is so important for the potential savings in time, effectiveness, and mental health, that it’s good to give it an article of its own.

Why should I even bother delegating?

As hinted at briefly above, delegating can be beneficial in a number of ways: for example, you can get things done faster if you delegate parts to others and then bring together the whole project for a client. This also makes you more effective, focusing on what you do best (and can charge for the most), outsourcing tasks that take more time and bring in less money to others who are happy to do them (often quicker and for lower pay). It may also save your health in the long run because trying to do everything yourself is stressful.

Do you trust me?

Above anything else, delegation is about trust. If you don’t trust the person (or agency) to do the job as well or better than you need it to get done, there’s no point in delegating. And if they in turn don’t trust you to pay and treat them as they expect (or better), they will let you down at the moment you can afford it the least.

Trust very rarely happens from Day 1 but is instead earned by both sides over time. To do that, establish very clear communication and expectations from the very beginning. Expectations should never be one-way demands — make sure to lay out what they can expect from you in terms of pay, instructions, timing, margin of error, confidentiality, contingencies, and so on. When building trust, surprises are a bad thing. So try to cover everything early on and make sure you both feel free to honestly communicate and ask each other anything. The worst scenario is when either of you has a reason to hide something, lie, etc.

Delegate the delegating

Ready to go right into Level 2 of delegating? Delegating is hard for many people (speaking from personal experience here) because people management is a hard skill and isn’t for everyone. Luckily, there are people who are absolutely brilliant at being organized and organizing others. Hiring one of such people to delegate your delegating can be an effective (and health-saving) ninja move even early on.

The Queen’s Gambit

Moving on to the strategy part, it’s not as simple as “how do I make as much money as possible?” but rather can take many paths. Start with your goals. If your main goal is indeed to make as much money as possible, then break that down into:

  1. Long high-paying gigs or cheaper quick ones?
  2. Ultra-specialization in something you do best or broaden your services to capture more demand?
  3. Chase clients at every budget level or hold out for the ones willing to pay you the big bucks?

But what if your goal is to have more free time? Then it may be a more obvious choice to focus on higher-paying clients with shorter gigs, for example. What’s your annual/monthly budget for a minimally comfortable lifestyle? Maybe your goal is to have more flexibility with your day, in which case it would be a good idea to delegate to people in different time zones.

Maybe, you really do want to open your own agency in time — and this is a good way to ease into it. In that case, you may want to slowly build a network of people to delegate to, making sure that it scales well, can function well with minimal oversight by you, and that people work well with each other.

The takeaway

Delegation starts with on builds on trust. Take your time, find the right people, and be strategic early on about your goals. Remember the difference: strategy is your overall journey while tactics are the ways you’re getting there.

And… action!

Let’s put this into action. Answer these questions as best you can by actually writing the answers down:

  1. List your top 3 reasons for delegating in order of priority.
  2. Think of what someone can do to show you their trustworthiness? What can you do to show yours? Feel free to make lists.
  3. Take an honest assessment of whether you are a person who loves organizing and managing or not. Can you think of people in your life who are?
  4. What is your big goal? If you start delegating today, where do you see yourself (and your work) in a year? 5 years?
  5. Answer the three questions in the “Queen’s Gambit” section.
  6. What monthly income do you need for a comfortable lifestyle at this point in your life? What about in 5 years?

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Dream Team

The best freelancers in the world — building award winning interfaces for today’s most innovative companies.