Leading Your Startup Team Through the Trenches

4 min read · 7 years ago


As leaders, it’s our responsibility to orchestrate our team’s activities to achieve desired outcomes. Many of us macro-manage to unlock our employees’ capabilities. But to be an effective macro-manager, it is essential that we know when to interject and disrupt our team’s direction, and when it is appropriate to step out of the way and let them do their thing.

One key strategy to help us know when to interject is to observe the operating environment surrounding each of our teams. To illustrate this strategy, let’s simplify our world into two types of operating environments: low morale and high morale.

Through observation, you can orchestrate a change in tempo by going against the grain and acting in an opposite manner of those who surround you.

Low-Morale Environments

When the chips are down, melancholy, despair and doubt can creep in like a shadow throughout your organization. When your technology systems have an outage or a sales deal didn’t pull through, people lament. It could happen over a month or it could happen in a span of 30 seconds. Either way, your team is likely making silly mistakes due to a lack of attention to detail. They are also at risk of missing growth opportunities because their energy level simply doesn’t motivate them to identify and pursue those opportunities.

You aren’t immune, so you’re undoubtedly feeling the same way. But instead of caving into those feelings, recognize this as a signal to act differently and set a new precedent. Give compliments, cheer team members on, keep a smile on your face, and speak about when you’ll get that deal and when you’ll have the systems back up and running at peak performance. You could even hand out rewards or awards for small accomplishments.

I used this approach during my early years working in Walmart’s Information Systems division. In the early 2000s, SamsClub.com was operating on an antiquated software platform. We were impacted by multiple system performance issues that caused website downtime and slowness approaching the holiday season. Our minds and bodies fatigued and our moods worsened, which only paved the way for finger-pointing and increased human error. Our leadership team was determined to improve our behaviors and consequently we were able to secure the systems before it mattered most.

By acting contrary to how your environment would pressure you to act, you can quickly lift your team out of this dangerous scenario and get them back on track.

High-Morale Environments

When everything is going correctly, exuberance, triumph and exhilaration can gleam throughout your office. When profits are high, your team receives a reward or a project finishes early, people celebrate and euphoria overwhelms the team mentality.

This is also a time where strong leaders must accept the reality that this is not a sustainable operating environment. In this state of high spirits, unsavory behaviors have the potential to settle in, like complacency, lack of attention to detail and disregard for proper due diligence. People will more frequently “shoot from the hip” rather than make sound business decisions.

In this environment, you need to keep people grounded and focused. Remind the team that it’s a slippery slope and that they should use this time not to celebrate, but rather to plan and prepare. Now is the time to secure critical parts of your business, plan for bold strategic decisions and parlay this success into more success. Don’t let people off the hook (even for small timeline misses or minor quality issues); hold them accountable to the little things. By requiring a higher level of execution before handing out awards or rewards, you will demand greatness instead of “goodness.”

We experienced this scenario a few years ago at my company Echidna Inc. After our initial years brought immediate business growth, many of us were delighted and lost focus as a result. Our leadership team quickly tightened the screws on ourselves and our teams before this complacency could cause long-term damage. This significant increase in focus enabled us to continue our success and build on it in the coming years. Instead of giving into complacency, choose to act in an opposite manner by using your recent success as a catalyst for greater future success.

High- or Low-Morale Environments

Your sanity is paramount. An old saying reminds us to be “never too high, never too low,” and I use this as a way of keeping emotions in check. Remain grounded, focused, stable and prepared to take on whatever highs and lows come your way. Choose to be a stalwart for your team so you will be viewed as the rock that they can lean on in both good times and in bad.

The key to effectively doing this is to focus on being aware of your emotions: practice being objective about what you are feeling. With practice, you will be able to detect when you are overly excited or underwhelmingly distraught. Use this as your trigger to act in a contrary way. If you detect that you are overly excited along with your team, then take a deep breath, evaluate your risks and opportunities and focus. If you share in your team’s downtrodden spirits, force a smile on your face, pat yourself or someone else on the back, and find the little wins.

This philosophy will prevent you from falling victim to the “pendulum effect,” which occurs when you are extremely high for a period of time, then a shift of events plummets you into an extremely low place, and so on. If you lead this way, not only your stress level with be sky high, but your team will be confused by your inconsistent behavior.

My high school basketball coach taught me these lessons at a very young age. They worked for me as a teenager as I was dealing with the highs and lows of learning what it was like to win and lose, and more importantly, as I learned how to lead through those times. I’ve found it to be useful throughout my life and my career, from leading a Fortune 100 company with responsibility for a nearly $1 billion business unit, to building a startup team from scratch to eight-figure revenues.

Find time to celebrate, and to grieve, in balance. If you act contrary to how your environment is encouraging you to act, you’ll become the stabilizing force that keeps your team positioned for sustainable success.

Adam Roozen is a former developer, marketer, and program manager and continues to be a successful business builder and leader. With roots in small-town southern Minnesota, he gained his corporate chops at the Wal-Mart Home Office leading marketing and operations for Samsclub.com, and is currently CEO at a leading eCommerce agency, Echidna, Inc.

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