Four signs that it's time to grow your team at work
And five things I've learned about having free time
Happy belated Thanksgiving! I’m back after taking a break last week for the holidays. I’m going to split today’s post into two very different topics:
How to know when to grow your team at work
Some gap year reflections on having free time
How to know when to grow your team at work
This is a huge question! I’m going to focus specifically on this question in the startup context. This was a question we thought about time and time again at TestBox and it almost always felt like we were either hiring too early or too late, and never perfectly on time.
From a runway perspective, it’s probably a bit better to hire too late, but that also means that in the interim, you’ve stretched your team thinly and risk burnout. (Or it may mean you’ve compromised on the quality of output.) Tl;dr here is that I think there’s no right way to do it and it’s up to each person to weigh the pros and cons based on the specific context. On a related note, I have many thoughts on hiring right and also embodying the hire slow/fire fast philosophy, but I’ll save those for another day.
Before you even get to hiring and firing, you first need to know that it’s time to hire. Over time, I’ve seen four key indicators that may point to a need to grow your team:
Someone on your team keeps saying, “I don’t have time to spend on the most important projects/efforts/work”
Someone or multiple people on your team are wearing multiple hats and their day-to-day no longer reflects their job description and core role and responsibilities
There’s a lack of process and structure that’s leading to inefficiency and sub-optimal output across the team because no one has time to figure it out
The team is working effectively but you’re still not getting the output you need on the required timelines
I’ll share a few examples from various startups I’m familiar with to illustrate these indicators.
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FIRST: Time to hire a PM
A team with many software engineers and a designer, but no product manager.
Either one of the lead engineers or the designer begins to spend a lot of time on process, scoping out tasks, assigning tasks, writing or revising product requirements documents and/or specs. Suddenly that person isn’t doing the work they were hired for. The designer isn’t getting time to do user research and validation, or feature requests aren’t being prioritized and they’re just being tackled. The lead engineer isn’t coding and/or focused on mentoring the rest of their team.
In an ideal setup, each person should be doing the work that they are uniquely equipped to deliver – that’s the whole purpose of having different roles and responsibilities in a company. Very few members of the team should be generalists, and the way each person spends their time should be tightly aligned to their unique skillset. In this scenario, hiring a product manager would probably lead to better processes, higher efficiency, and better prioritization.
SECOND: Time to start your Marketing and/or Sales team
A team with just one marketing hire, but no one in sales, or vice versa.
This person is no longer just managing the marketing funnel but also handling inbound calls from prospects. Or on the flip side, you have a sales leader who starts to spend a lot of time managing conference sponsorships and measuring website traffic and directing the team’s marketing messages in addition to managing a SDR and taking calls with prospects. In both scenarios, those individuals are being pulled away from the high value activities that they need to be doing.
THIRD: A well rounded team that’s stretched thin
Your team is well rounded but everyone is consistently working extra hours, feeling like they have more on their plate than they have time for. With traction and customer demand, this isn’t sustainable.
The quick checks here are:
Make sure that there are processes in place so things are efficient and orderly (the lack of process/order can also lead the team to feel this way, but in this scenario, hiring more people wouldn’t solve the issue unless you hire someone to specifically implement process)
Confirm that the team is being given focus time to work (rather than in meetings or dragged down by other bureaucracy/overhead), and somehow they’re still not getting all the work done
Other signs can be when maintenance issues start to create big disasters or bugs are piling up. In this scenario, it may simply be time to hire more of the same role to get more work done. Generally, this is probably a time to hire more software engineers, though it could also be a time to hire more people for your ops team if you’re an ops heavy company.
One important caveat here is that if the driver behind the need to hire is primarily customer demand, it’s important to forecast that demand and wait a few months to make sure it’s long-term, sustained demand rather than just a spike. It can hurt a lot to hire a full-time team member (or multiple) if it’s just short-term demand.
FOURTH: A lack of a clear leader for a specific team
A team where a lot of time is spent making decisions and debating pros/cons.
This is likely correlated to not having one clear leader and lots of senior team members who are going head-to-head against one another. In this scenario, it may make sense to hire in a head of that team to make the calls and cut out a lot of the back-and-forth. This isn’t to say that the opinions of the senior team members don’t matter, but rather that there needs to be someone with final decisionmaking power. This can happen to any functional group, but is a common problem when startups first kick off and don’t want to hire any heads of departments before the departments are at least slightly built out.
Five things I’ve learned about having free time
ONE: Chores and other miscellaneous life admin can take up infinite time
My more experienced gap year friends warned me about this, and I have definitely experienced it firsthand. Sometimes between meal prep and grocery shopping and cleaning/tidying up and life admin, an entire half day would disappear, if not more. Throw in laundry and then the whole workday was gone by the time I sat down to be idle. E and I have discussed this a lot and we’ve tried to find a balance where I still take on more of the chores but I timebox them or save some of them for weekday evenings. For me, getting out of the apartment has also been very helpful because then I can be 100% focused on other activities and there’s a much smaller chance of being distracted by life admin and chores.
TWO: There is value to having weekdays and weekends even if I am not working
Likewise with holidays and vacations. Last week, I fully embraced the holiday week. I let myself spend entire days prepping our Thanksgiving meal and hanging out with our friends. I made a conscious choice not to worry about having other productive pursuits that I try to keep up in my new “normal” gap year weeks (such as newslettering or reading). Incidentally, I learned that I derive a lot of fulfillment from preparing food for friends and family, because there was a day or two last week where it felt like all I did was cook. Instead of feeling exhausted or frustrated, I felt really, really content. (I will insert here the classic gap year thought of “Should I be a <blank> based on this week’s experience?” According to this data point, maybe I should pursue being a personal chef…)
I enjoyed giving myself a break from pondering the big questions of what I want to do with my career and where I want to go in life. It made me excited to get back into my own flow by the end of the week off.
THREE: I have discovered when I like structure vs free-flowing time
So, here’s a little update: I started doing Fractional COO work for a startup. I didn’t intend to actively seek out opportunities to try out this career path quite yet, but opportunity came knocking and I was very intrigued by the work. I’ve been doing a few hours each week for the past few weeks and it’s been the perfect amount to keep me mentally engaged and challenged without taking away from the free time I’d like to enjoy.
As I started doing this work, I have picked up on how I naturally like to organize my calendar. I like to leave my mornings mostly free until 11am so I can be lazy and slow as I wake up, do my morning exercise, pitter patter around the house tidying up, and scroll some Reels and TikToks. I don’t mind if there’s an 11am meeting on my calendar but anything earlier definitely weighs on my mind the night before. (I am not a morning person when left to my own devices though I’m pretty high functioning if I have to wake up early, as long as I sleep early enough…)
After lunch, I like to have a few hours of specific activity time. Sometimes that’s working on my newsletter (like today!), having meetings/calls/catchups with friends or doing asynchronous work for the startup I’m working with. I also enjoy using this as a window to get out of the apartment and settle down in a cafe somewhere different.
As it starts to get dark, I like to have free-form time – sometimes I run errands or start to prep dinner slowly, and generally this is when I enjoy an episode or two of TV. After dinner, E and I tend to have a shared routine where we go for walks or do other activities in the city, or we’ll tackle some life admin together. That part varies more but always has been varied even while we were both working.
All of this is to say, I think crafting a routine that works for you when you have control over your calendar can be a huge factor in happiness and productivity. It may take a while to find that routine and it will require tweaking from time to time, but it’s worth it to invest in figuring that out.
FOUR: It can get lonely during regular working hours
The first few weeks of my gap year, I was really excited to catch up with old friends and scheduled a ton of catchup calls. I was actually pretty overwhelmed by all the socializing and then by the third week or so, I had a pretty sparse calendar and realized I felt quite the opposite. I was suddenly really hungry for conversation and social interactions, and that’s when I realized that I should space out my catchups.
My approach so far has been to have no more than two calls a day and to leave 1-2 days a week where the calendar is fully empty of socializing, so I am forced to sit and reflect. I’m a firm believer that it’s okay to feel a bit lonely at times and it’s important to understand that feeling and be comfortable with it, but also that I shouldn’t let myself fall into deep social isolation either.
FIVE: Some things are just not that appealing to me even when I have tons of free time
There are a lot of backlogged plans I have for myself. Like topics I want to spend more time reading up on, YouTube videos that I’ve bookmarked, and long-term projects I thought I wanted to pursue. All that said, I have noticed that even with free time, I haven’t touched a lot of those items. I’m realizing that there are themes to where I tend to gravitate: reflecting, organizing, writing, strategizing, and optimizing are some of the things I find myself doing the most. It’s what makes me the most curious, excited, and satisfied. I’ve started to realize that if I have to force myself to spend time on something on my backlog list, it’s probably a sign that those are not the right areas to invest in if I’m trying to align what I do with my passions and innate curiosities.
Part one of today’s newsletter covers when to know it’s time to hire extra people for your team in a startup. I share a few examples and indicators to look out for to know that your team is stretched thin. Part two covers some of my reflections on having free time. I’ve learned where to timebox myself and how to structure my time to optimize for productivity but also enjoyment.
In two weeks, I’m going to talk about a question that came in from one of my readers about how I handle failure. As always, drop me a note if you have questions or suggestions for topics for me!
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