Multiple Hat Syndrome Part II: When It’s Not Just You Anymore
By: Janice Chan
Tags: Collaboration, Nonprofit, Hiring, Freelance, Agile

Five hikers walk up a gentle hill with tall grass, silhouetted against a dusky blue sky. | Photo by Tobias Mrzyk on Unsplash

Congratulations! You’re finally getting some help with your multiple hats and getting to delegate some of those hats that have become, well, old hat. At last, you can focus on — hey, wait, not like that; no, that’s not, you’re doing it all wrong!

Anyone who has ever passed the torch at work (and anyone who has ever had to pick up somebody else’s mantle) knows there is all sorts of implicit, institutional knowledge that often gets missed in the hand-off. It’s natural. After doing something for so long, we forget what we know that others don’t. We forget the things we used not to know. If you haven’t heard of a nifty concept called knowledge management, now’s the time to learn more and to get it in place before you need it.

Now there’s a lot that goes into any transition, but there’s even more change to deal with when you remain involved but are beginning to delegate some of your work.

Yeesh, it was easier just to do it all by myself!

When you’ve been wearing multiple hats and start to hand some of them off to other people, you’ve got this issue multiplied. Not only do you have to remember to pass along that implicit knowledge about wearing a particular hat successfully, you also need to remember to loop in extra people that you didn’t have to before when it was just you.

There’s a learning curve for working with anyone new to you or even with the same people in a new capacity.

This is natural. There will be growing pains. Don’t take back the reins just yet. It may take longer now, and you may need to fix some things, but there is a benefit to letting others (and ourselves) work through this learning process. (Apparently this works on kids, too.)

And that benefit is that you get the support you need to do what you excel at. You will get that time back in the long-run, and multiplied. That’s the power of working together. Isn’t this the ethos of working at a mission driven organization? And yet…. *commence the teeth gnashing*

No, it does not have to be so hard.

There are some things you can do to hasten the ascent up the learning curve.

Call out communication preferences.

If you’re having a hard time getting explicit about this because, well, all of your conversations were previously in your own head, try this:

Draw out the different hats (or simply write out the roles) on a piece of paper. What would you have wanted to know before accomplishing the associated tasks? What were things that might change that you would have wanted to know about?

This isn’t an end point but a starting point. You can share this list (or these lists) with the others you are now working with and see what else they might add, what other preferences they might have.

It’s not only about communication, of course. There’s also a new power dynamic.

When you were wearing multiple hats, even if you had a boss or other stakeholders to whom you reported or who gave final approval, you still chose in which order you wore your hats, how you proceeded, who goes first, etc. Your meeting of and management of the minds was all internal.

One of the hardest things about delegating is feeling like we’ve given up the control we once had in the process. Which is not untrue, but it’s not particularly helpful to think of it that way.

Think of it as a way to clear space in your head to focus on what you’re doing now.

You can’t do that if you’re constantly worried about all of your old responsibilities and making sure they’re getting done. The first step is to acknowledge the control issue. The second step is about the structure that will support your communication as a team.

Discuss how you will work together and what this physically looks like.

When you were a kid and first started being allowed to go places by yourself, did your parents say, “Okay, cool, see you when see we see ya”? Maybe they did, but I’m willing to bet most of our parents wanted to know where we were going and when you would be home, might have had us call when we got to our destination, or at least to let them know if we were not going to be home for dinner, and so on.

As it has done for parenting, technology has evolved and there are more ways to put our minds at ease than requiring that people carry quarters every where and also without calling them every five minutes. (Because, you know, that defeats the purpose of delegating.)

How will you work together and keep everybody informed of your progress? When are the check-in points? What happens when there is an obstacle, a major change, or when you simply have a question? Where are the shared files that everyone is working off of and how are they organized? Is there a team calendar? Does everybody have the access they need?

Ahoy, the future of work, which includes distributed teams. Maybe there’s a Kanban board so everyone can see what’s going on and where everything is at (and where you can see red flags) as well as a backlog for future projects. Maybe you have daily or weekly check-in meetings. Maybe there’s a team calendar with deadlines, editorial dates, organization events, and vacation days. Maybe everybody’s collaboratively editing documents online or there is one person in charge of the master spreadsheet. Perhaps there are designated milestones for evaluating progress and adjusting course if need be. A lot of this is basic project management, but it needs to be revisited every time the team changes.

And speaking of project management, somebody needs to wear the hat of making sure everybody is working together and progress is made.

But collaboration can’t do it all. Discuss decision-making before any decisions are made.

What will be decided as a group? Which decisions require consulting the group but are still made by one owner? What decisions can be made by each team member individually? Which decisions does everyone else need to be informed of?

Sometimes people will defer to the person who used to wear that hat and will wait and wait when you were expecting them to move ahead on their own. Sometimes they won’t when you expected them to consult with you first. Either way, it can cause all sorts of tension. There may still be some tough choices and not everyone will be happy with every decision. But you can prevent a lot of confusion and chaos by talking through the decision-making process and who owns which decisions ahead of time.

Build in times to make sure this way of working is in fact working.

Every team takes time to gel and find its rhythm. Sometimes that means you need to try different methods of communications, have more or less meetings, or that you may just need to adjust the way of working during certain parts of a project, or around certain events or times of the year. But it’s also very easy to get derailed and for nobody to say anything for a while if they’re worried about disappointing you. Reduce the barriers and ask the question as a default. Wethos has a great working in system in place helping their nonprofit organizations benefit from distributed teams.

Over time, as your parents learned to trust you, they probably eased up a bit or gave you a bit more freedom. Not that delegating is the same thing as parenting, but sometimes responsibilities that used to be ours feel less like hot, smoky torches to be handed off as quickly as possible and more like our work-babies, if you will.

It takes time to build that trust with new teammates, whether they are coworkers or a team of freelancers, but it also gets easier and better over time as you learn to work with each other.