Too Many Hats: Managing what you need to do at a startup when what you need to do is all the things


That picture is overused for this topic. But I’m sorry, it’s hilarious.

I haven’t posted in a while. Sometimes life gets in the way. And lately, that has come from the age-old startup problem of wearing too many hats.  Large companies have separate departments for product, engineering, marketing, sales, customer support, operations and purchasing, finance and accounting, etc. Each of those departments probably has multiple people with even more defined roles. At an early-stage company, you throw in fundraising as an almost full-time job and then you have employees that have to take on the entire responsibilities of multiple departments.

Don’t get me wrong, that’s a totally expected part of the job and I absolutely love it. I want to be involved in all of those things and I probably wouldn’t be happy if I only worked on one of them. That was one of my initial draws to product management. Even if you don’t directly work as a marketer or a salesperson, you still need to work very closely with those departments and many others. You need to understand their work, what drives it, and how to best get things done.

But yeah, it’s gotten to the point where I keep a Google Doc listing my current job responsibilities which I update and re-prioritize weekly.  My current, prioritized roles include:

  • Ops manager. We just started shipping our first commercial product and I’m in charge of managing component inventory, manufacturing (in-house and outsourced), shipping management and scheduling, and forecasting and fulfilling inventory needs based on our sales pipeline.
  • Customer success manager. After deployment, I’m responsible for helping customers reach their intended goals with our product and expand their use in the future. I help solve issues that come up and act as the main point of post-sales contact.
  • Marketing manager. We’re at a point where lead generation is getting more and more important. I devised a content/inbound marketing strategy and am the main person responsible for creating interesting and insightful content that drives people to our website and eventually to our sales team.
  • Business development. Identify new potential markets for us to expand to, build contact lists, and identify partnership opportunities. A big, planned part of our business relies on partners that see us as a value-add in their work and can help convince clients to pay for it.
  • Product manager. It’s a little sad that this is so low right now, but realistically our main goal is shipping the finished product, putting the final touches on our software release, and performing maintenance. But we’re still trying to look towards the future as well. And this means I need to work on our product strategy and roadmap, validating product ideas with customers, conducting user interviews and testing, designing and updating user personas, building product requirements and wireframes, and building business cases for potential ideas.
  • Engineering/project manager. We try to run Scrum. I don’t know how successful we are, but we try. I manage this process as Scrum Master and project manager to make sure we can hit our deadlines and deliver to clients.

In the past, roles also included mechanical engineer, intern manager (which is coming up again this summer), technical sales, and 3D printer technician, among other things.

I don’t mean for this to be like, “Oh look at all this stuff I do!”.  But it’s more like realizing, “Wow, there’s a lot of stuff on my plate. How do I manage all of this while doing good work?”.  To be successful, I’ve had to explore ways to manage all the different work required of me and the company in general.  That’s what I really want to talk about in this article.

Wearing all the hats and still rocking the outfit

The key to managing all the different tasks, at least to me, is to start big and go small. Find out what needs to be focused on, and eliminate the clutter so that each day becomes more manageable.  Regularly take a step back, take stock of what is important to the company right now and what that means for your role, and re-prioritize as necessary. Don’t be afraid to hit pause on things or throw them out entirely. The sunk cost of work that’s been partially done is nothing compared to the cost of doing the wrong things now and in the future.

In general, I try to do things that help me manage my week, my day, and each task. Each one informs usually helps inform the next. There are many different ways to manage your time and priorities, but I wanted to share one thing I do for each.

Weekly: Prioritize each week with themes

The most important thing I try to do is make sure that I give myself enough time and focus to make sure that I can truly make an impact at my work. Yeah, I listed 6 different roles above, but if I spent 1/6th of every day on each role it would be nearly impossible to make tangible progress on anything.  Real progress comes from being able to throw yourself at a problem without distractions.

To help with this I borrow a bit from Scrum philosophy. The building blocks of Scrum are user stories. User stories are self-contained units of work that represent real progress towards a feature or outcome. Typically they are presented as:

As a _(specific type of user or stakeholder)_, I need to _(perform an action)_, so that I can _(gain a specific benefit or achieve an outcome)_.

Sometimes, the goal may be something that can be worked towards through many specific stories. This is where themes come into play. Scrum alliance uses the example of improving the performance of a feature as the theme Performance Tuning.  There are several different things that could be done to incrementally improve feature performance, but each represents work in a different area of the project. Several user stories are written and completed during a themed sprint with the aim of improving overall performance.

As a bonus, themes also appear in product management for road-mapping.

Applying themes to work

I apply this strategy by beginning each week with a theme assignment exercise. I look at what really needs to be done to create the right outcomes for the company, and I prioritize on one or two areas of focus. That’s not to say that I don’t do work on my other roles for that week, but I pick one main hat to wear and put on the others as needed.

So one week might be Marketing-themed, where the goal is to create a bunch of content to draw people to the website, work on our monthly newsletter, make website updates, and do some PR outreach.  Biz Dev Week means diving deep on research in a few markets, learning how much of an impact we can make on them, finding the right contacts, and exploring partnerships.  The past couple of weeks have been Ship Weeks. Above everything else, the focus is on assembling product, testing it, and shipping to customers. When that’s done, other items can be worked on.

Within the framework of our sprints, I will prioritize my personal backlogs accordingly. I create a to-do list for that week’s theme with items that will drive the business forward in that particular area.

Another option: systems thinking

I won’t go in-depth here, but another great tool is combining stretch goals with systems thinking.  I use this more in my personal life, but it can get frustrating feeling like you never get any closer to that far off goal in the distance. Systems thinking give you things to work on every day, and if you’ve done those things you know you’re progressing towards the goal.

Daily: Prioritize each day with the Rule of 3


So now there’s a plan for the week, but then life happens. Emergencies come up, fires need to be put out, and real work can fall to the backburner. It can be tough to get back to center and tougher to feel like you’re making real progress. One way to combat this is to refocus yourself at the beginning of each day.

A great way to accomplish this refocusing is by using the Rule of 3. The Rule of 3 is pretty simple, but can absolutely change your day.  It makes it easy to know what you want to do, to feel like you’ve spent the day well, and to say no to the distractions that come up.

Applying the Rule of 3 to work

To use the rule, you simply:

  • Begin each day by reflecting on what to focus on that day.
  • Write down three things you want to accomplish today.
  • That’s it.

There are some tricky parts here. First, you need to make sure each task is actually something that can be accomplished in one day. This might mean breaking down larger projects into sub-tasks.  You also have to know when each task is complete. Vague things like “work on market research”, don’t lend themselves towards knowing when you’re done. If you define what it means for each task to be complete, you know when you can put it down and work on the next one.   Finally, sometimes things come up and you might forget what your 3 tasks are. Make sure to write them down and consistently remind yourself of them during the day. When you ask yourself if you remember what the 3 tasks are, you can also ask yourself if what you’re doing right now is contributing towards them.

I try to do this every day and write down 3 things to accomplish at work and 3 things to accomplish in my personal life. It’s a great way to keep myself from plopping down on the couch and wasting my night on TV or video games. It’s very helpful towards making progress on my personal goals as well.

Another option: whiteboarding the week

This ties in with systems thinking, but I find that it’s incredibly helpful to make sure your goals are staring you in the face every day. I use a whiteboard to lay out my systems and then I have a weekly calendar where I check off if I’ve achieved the system task for that day.


Some weeks aren’t the prettiest but that’s okay.


Per task: Cut procrastination with the 5-Second Rule

No, not that 5-second rule.

Easily the biggest obstacle to progress for myself and many other people is procrastination. Particularly I struggle with it as a way to deal with feeling overwhelmed. I’m lucky in that I generally deal with stress pretty easily and in healthy ways, but sometimes that best thing to do, when you need to do everything, feels like doing nothing. And these days there is so much happening that procrastinating is easy. In the past couple years, I often find myself looking at political news because there’s bound to be some new big thing that has happened since I last checked 5 minutes ago.


So the key is finding ways to beat procrastination. Finding ways to get yourself started. The 5-Second Rule is great for this.  It breaks the typical cycle where you think of something you need to do and then your brain comes up with excuses for why not to do it. It breaks the tendency towards indecision.

Applying the 5-Second rule to work

“If you choose not to decide, you still have made a choice”

– The Holy Triumvirate

This is pretty straightforward. When you find yourself needing to do something, simply use the “5-4-3-2-1” countdown and then act on it. I like to add “blast off” to the end because it’s fun.  The best time to use this is when you realize your brain is starting to come up with excuses to procrastinate more. “Oh I’ll just read one more article and then I’ll get started” turns into “Oh I’ll just — wait, no…..5-4-3-2-1-Go!”.  Every day is filled with these moments when you can kickstart yourself. Right now my major application for this rule is trying to get out of bed early instead of snoozing the alarm.

Another option: the Pomodoro technique

The Pomodoro technique is a way to keep yourself from burning out, which to me is when procrastination strikes the hardest. The goal is spend 25 minutes in deep work on a task, then take a break. The break lets you step back and reflect (usually subconsciously) and the work and helps you realize the best things to do. It also gives you something to look forward to. I use the Tomato Timer!


Hopefully, these have given you some good insight into options that you have. Do you have different strategies that you use to manage your workload and get things done when there’s so much to do? I’d love to hear about them! I’m always looking for new things I can try and improvements I can make.

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