Delegation… fast and slow

Delegation is a constant struggle. Many times I have ended up taking a step back to take a step forward. I have found I have done a better (but slower) job at work than at the charity. Potentially speed is directly correlated to a successful outcome. So I have tried to look at what helped and what certainly didn’t.

Let’s be real – at first, I just did not want to delegate.

I moved from Investment Banking as I got more senior partly because I just loved my analytics too much and I could not conceive covering clients without having built a model and everything that goes with it. I hoped that would never go away. And it was tough to find a balance, as eventually, I did have to move away from doing all the numbers. As I focused on strategy, business analytics and lots of data, I had a hard time allocating my time in proportion with the areas I wanted to spend time on. Which really was strategy making with a fact-based approach. What I wanted was to know all the relevant facts (the word relevant is of relevance here), while connecting dots and challenging the status quo. I determined challenge was what I valued the most in my role, and I had to create the means to do it effectively and efficiently. The 2 don’t always come hand in hand, so I took the first step.

Make a plan

You could guess this one right? I am a planner. Indeed, that is the case but let’s face it, you need a plan to hire someone. You need to identify what you want to delegate, what skills do you need for your team, how many hours you expect someone to work, what would you be expecting of them. At some point, you will have to write a job description. A good way to start doing this is to look at the different areas of responsibility and what you are doing in each. In many new businesses, you are liking to be doing everything across the value chain. You may want to consider keeping a time log for a few weeks so you can understand where you are spending your time (really) vs. the areas where you think you are spending your time. And then overlay that with what you think your role should be and what your own goals for the business are. It was not until I accepted that I wanted to grow into a new role that I was more willing to let go and put pen to paper on drawing out a team for me.

Last year, I had the intention of really moving away from the finance analyst responsibilities, which I still kept, mostly out of legacy and also because they were so comfortable for me to keep. However, I knew I could not become a real CEO by being so ingrained into transaction bookings. I needed to see the reporting, but not doing the reporting. With that, I laid out all the tasks I did monthly for receipts and payments, all the account controlling, common mistakes, existing files, all repeat and ad hoc processes I could think of. It ended up not taking me that long and it was the envy of other members of the team as it suddenly was so clear that I needed a full-time person to cover all these responsibilities. I also included in that taking away some of the tasks that were burdening the 2 other members in the team, to allow them to focus more on field work or donor interaction and focus all finance controls in an independent function that would report to me. I am pleased to report success (though not full transition yet) and whenever she starts getting bored or less busy, we go back to the plan and check what is next.


I know – obvious right? That means you will be willing to let go and jump right out of your comfort area. If this is the first time you are doing it, it is pretty much like jumping into the abyss – that first time you outsource that analysis that you have always done, the first time you don’t run the numbers that you are bringing into the next meeting. So you need to hire consciously to what is it that you need help with. Hiring your copycat may not always be the best outcome, though I have a history of doing that more than once. I have done so on occasions because I knew I had to replace large parts of my job to step up. That required a similar skill set to mine and that was the only way I was going to be comfortable with it. But as the team expanded I focused on ensuring the skillsets can address the diverse skills of our growing responsibilities. And on hiring people that can do and like to do things I don’t know or don’t like to know too much about, When you have trouble describing all the 10 areas you have responsibility over and lack time to focus on the important as you spend too much time producing data and not enough time thinking about it, hire it is.

So fine Sara, I have hired. But it just does not work; they can’t do what I do and it all ends up in tears.


If you have done a good hire, you have likely hired based on skillset and the person may not have experience in a similar role. Chances are they have relevant experience, but they have never done what you do. Yes, you have to teach them. I see there are 5 key areas of learning:

  • Values – first and foremost you want to teach people what matters to you as a leader, as well as to your business and clients. If I value challenge, I will work with the team on not taking any data for granted, will foster a culture of questioning, including to ourselves, will teach how to develop relationships of trust with people you constantly challenge as well. I don’t have a manual, the values can only be taught by role modelling, there is no ‘do what I say not what I do’. You can speak about them but your daily actions will have to speak louder. Now, I know in today’s world there is an increasing trend to hire remotely, and that makes this point very hard. I have that at the charity – but the only thing you can do is to model all of your interactions on the values you want to inspire;
  • People – people is what is at the essence of any business, whether we are talking business partners, other employees and most importantly your clients. You have to explain who the people in the business are, what they do, how they think, how they may prefer to interact, what challenges they are faced with. This will require good communication, still not a manual. It is not learning by doing but rather take time to prepare the meeting (or debrief) with each new stakeholder including some background information that will help your new hire be able to connect with the person on the other side of the table;
  • Business – I know you want to go straight to tasks and work done, but you also have to explain to your new hire the business, how you make money, how it works, where do you want to go to. It can be your vision if you so want to call it but it is more than that. It is to explain what is important in the business, what products you offer and who do you target, what are the critical success factors, what are the key risks to watch out for. All this will make the person capable of helping you better in a way that you can trust is aligned with the business interests;
  • Job – this sounds obvious, and hopefully you have explained quite a bit when you were doing the selection process. But it is also true that a job description is not necessarily as descriptive as it could be, and many concepts don’t mean anything until someone is actually on the job. You will need to be clear on the goals for this job, what you expect the areas of responsibility are. Whether the person has experience or not, it would be a step in the right direction to assume they know what to do, as they applied for the job. It is often the case that the business evolves fast, and that a lot of the topics you chose for your job description are no longer relevant, or really mean something else. Be sure to continuously be clear on expectations and don’t take misunderstandings personally – just clarify and move on, especially in the early days;
  • Technical – this was the one you wanted to start with, but I leave it to the end because left in isolation it will be hard to make this hire work. It is critical that you teach people how things get done – if they don’t know how to check data, run an analysis, build attractive marketing materials. All this can be taught and it is down to spending time with them, at first having them shadow you, other times letting them give baby steps and then go through it in detail with you. Sometimes, you will still run the tasks and speak out loud as you do them as to explain the rationale of your choices. One thing to bear in mind – watch out for suggested alternatives, nothing tells you that it is your way or the high way. What I found last week (painfully), was that I had likely done points 1 to 4 but was still not complete on technical and jumped straight to execution. I had to step back and accept that my analyst had not yet done closing of accounts with us, she was straight out of Uni, and even though she understood what the goals were and how I like things done, it was still very hard for her to execute without some of the technicalities. So we had to do that, with me stepping back to teaching multiple year-end processes, documenting as much as possible as I went along, and ensuring I was explaining all the additions and changes we were making along the way. Time-consuming? Yes. Worth it? Absolutely.

“When you assign someone a task for the first time — with no prior training — simply because you are unavailable to do it, their chances of succeeding are slim. You also run the risk of damaging team morale. Employees might get the impression that they are not capable of doing complex work if they are too overwhelmed by the task”, HBR 2018

Ok, I planned, I have hired, and I do even have a small training program I run for people. I still can’t do it, I can’t trust them. I hear you, trust is the biggest deterrent.

Establish processes that create trust

Find out what type of manager you will be for each person. You will notice that I did not say “find out which manager you will be”. In fact, your management style will most likely adjust to each person as well (or it should). Some people will thrive on less guidance and more goals, others will need constant micromanagement and specifics on how to approach things (here is a good HBR article on it). What you want to do is ensure you establish the right set up so you can trust people, while still having enough check-ins to be confident what you need is getting done. You can have weekly check-ins, daily check-ins or ask to be copied on every email. Part will also depend on personality and what you are asking that gets done. No matter how much of a micromanager you are, at some point, you will have to let go of some of the details and become an expert at overseeing. This is something that can be learnt.

For me, it is easier at work. We all sit together, so I catch a lot of what is going on, and it is easy for the team to reach out with questions. I delegate over email or in person and tend to write down what each person is focused on for the week as well as what the next steps are on my side so I ensure to follow up as needed. We also got ourselves a whiteboard for the team with our biggest priorities for each week. I make an effort to be available for questions and when new projects come by I try to take time to go through deliverables with the team, draft out what I expect or show previous examples. I don’t always master it, but I find the proximity leaves the lines open in case of doubt. Also, mistakes are easier to catch and to follow up on in this environment. I tend to have a very immediate feedback culture in the team, which I sometimes have to tame, but eventually, it is key to allow us to very efficiently change approaches and get to a successful outcome.

It is undoubtfully more difficult at the charity, where I tend to work in a different time zone (the night shift) and they are in another country. Whatsapp has come along way in helping me manage this, but I recognise the communications process still has quite a lot of room to improve so that there are easy checks. At the same time, I have not established good enough oversight processes, so I tend to spend a lot of time on the details each time I am asked to verify something. The key reason is that I have not entirely completed point #5 above on teaching the technicals, and therefore I end up doing a lot of it myself. Because I do it in the evening I don’t have the heart to go back and ask for a repeat while having to wait for the next day. Last week, with the intensity of the days and nights we had, I was actually comfortable to do that, so I am establishing a fast response system with the team where in times like this when we are closing accounts, the first thing they need to do when getting in is to review what I asked or sent and address questions, so it can be done the same day and allow us to progress in tandem.

Are you done? This text is kind of long now. I could be, but I am not, so I have to add small bits


What do you mean, did we not cover teaching above? Yes, but this is not about teaching with the purpose of assigning work. This is coaching for growth and really allowing your team to grow with you. Be willing to create opportunities for them, give them visibility, assign them things you would enjoy doing but feel it can be the right thing for them to take a bigger step.  Teaching allows you to delegate your work. Coaching will allow your work and business to grow further. HBR seems to agree by the way (it is incredible the amount of articles you can find on delegation – seems to be everyone’s problem!)

Oh, and I forgot one last step. Delegate. It requires no further explanation

Photo by Carl J on Unsplash

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