Shane is me

Play The Long Game

June 05, 2023

The pressures of running a business will naturally bend you toward quick-win thinking simply due to the metaphorical fires all around you. Looking for the quick answer will often skew your priorities in ways that will negatively affect the people that work for you on a long timeline. This will naturally lead to consequences most of us have experienced at work: everything is an emergency, morale is low, poor communication, constantly losing your best talent - the list goes on. As a frontline manager I find that if you push back on the urge to optimize for quick wins, and focusing on the long game, what we know looks and feels like a bad work environment will start to fade away.

The foundations of my leadership training start in another life, long ago, with US Air Force officer training. I could write just as many things wrong with the authoritarian bent of the training, however they got some very important things dead on. They also take things much farther than your average corporate leadership training, and with good reason. Motivating people to put their lives in danger is much different from pushing code to production on time. If I can cherry-pick the things I find helpful from this experience I find a whole lot of leading by example, not asking someone to do something you're not willing to do, and taking the voluntary role of leadership as deadly serious.

The best leaders in the military, and in the civilian world, understand that it's necessary to earn the respect of your team. You cannot lean on rank and title to expect it. Only when you have this respect can you get the most out of a group of people aiming toward a common goal. Authoritarianism is a great shortcut to quick wins, but over the long term it wears people down like a sugar crash. We want to build people up and give them the confidence and trust to own their part of the effort. Teams must be shown a goal and let loose. By standing in the way, or by pointing where they have to go, you're assuming you know better than the people you hired to do the job you wanted them to do. You are not smarter than a team of ground level experts.

Life before work

There are some things that happen constantly, and the way my brain works I need to set up an algorithm to handle it. Given a problem with someone I manage, does it involve life outside work? Then life outside work wins. The scope and reasons literally do not matter because I'm thinking in careers, not quarters. Kid's sick? Take the time you need. Trip overseas for a few weeks? Have a blast and send pictures. I never think about a project that will be affected, or timelines that will need to be adjusted.

I don't like the term "work/life balance", because I don't believe they need to be in balance. Life outside work should take priority in every situation. You should put in the time necessary to be successful at your job and no more. If you have this mindset, and share it with the people that you manage, emergencies that pop up or time off aren't even a blip on the radar. If the current project is particularly important nothing models how much you're prioritizing your team's happiness like stepping in and helping get across the finish line when someone needs time off for any reason. In fact this is possibly one of the most visceral ways you can prove it.

If you show this every day then you'll be let on the inside of your team's lives. You'll know when they're in a difficult situation so you can better support them, you'll know the details of vacations, and no one will lie to you when they aren't feeling well. They won't feel stress when they tell you the good news that their family is pregnant, or they're unexpectedly becoming a caretaker. I think earning that invitation makes me a better manager because I get access to more of the person and their motivations. It also relieves stress in your team. It's so clearly a win-win that it astounds me every time I see it going wrong.

Bubbles, not shields

I've heard managers say that they like to, or need to, shield their team from all the crazy things that happen at the upper echelons of leadership. This comes from a good place, you want your team focused on the task at hand and not worried about things happening far above. Unfortunately, if your shield is too effective, it's only a matter of time before your team is shocked by something you can't shield them from; like a full and sudden reorganization for example.

I know that this is belaboring the metaphor, but I like to put bubbles up around my teams instead of shields. They're warm and comfortable within, but can still clearly see what's going on outside. I think it's a critical part of my job to keep my teams up to speed on what's happening up above and around them. This provides necessary context for them when these sudden emergencies tend to crop up, but mostly it's in the day-to-day that it helps when things like slight tweaks to priorities happen on a quarterly basis. A fully shielded person might get some anxiety when a project they're working on gets shelved for two quarters, but someone that's able to see outside the bubble gets a project deprioritized they understand the reasoning - even if they don't fully agree. This lets them make decisions in the long term about how to build things, or what compromises can be made for the sake of speed when things aren't going to be long-lived.

Teams of people tend to be able to make much better decisions than you can by yourself when they're given the entire context, and the reasons why we're doing all the things we're doing. Sometimes it's simple: we're currently focusing on projects that yield us the most money the fastest in our projections. Other times it's much more complicated and nets several full team meetings to discuss the nuance before making a decision. When these complicated problems come up, the team that's most informed will be the most successful.

You can create a bubble where your team is so well taken care of not only are they fulfilled in their job, but are actually happy to get started working every day. Your goal should be expanding that bubble with every opportunity. Share your successes, help and support others that are like-minded, and this will happen naturally over time.

Careers not quarters

"Not worrying about the deadlines passed down from above sounds pretty good, but that's not how it works in the real world." I'm pretending to hear you say.

There are millions of different companies and each has its own way of doing things. One thing that all of them have in common is the need to get more out of less. Getting people motivated to do their best work really is the best way I have found to keep a team operating at its highest potential. All of the things I've outlined here are what I would consider treating human beings like human beings, but this work has a wonderful side-effect of naturally increasing motivation through trust, empowerment, and prioritizing what's really important.

Once you have your team operating in such a manner by playing the long game, your teams will deliver more than you asked for and they'll come up with better solutions than the company asked for. Doing this consistently opens doors for you, their frontline manager, to have simple conversations with your peers and those above you about the project that's becoming larger and more complicated by the day. They're simple because your teams have shown that in spite of everything that's thrown at them they pull through every time.

Most people in tech have a tenure between one and two years - this is the exact consequence of quick-win thinking. Place where you care consistently in the right place: with the person and not with the business. You'll automatically start thinking the right way when you do. Instead of focusing on the short-term burnout for a quick-win that turns into a mess, if you're thinking the long game you'll find the team operating at higher productivity in the long term because they're happy. They're happy because you trust them, they trust you, they trust each other, and they know the why of what the company has asked them to work on. This is the work that it takes to earn it. You've got to play the long game.

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