Servant Leadership In Times Of Trouble

Servant leader, people-pleaser? Not so fast…

Omar Rabbolini
The Startup
6 min readFeb 5, 2020

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“It’s a trap!” Pete shouted before slamming his resignation on his manager’s desk. He was recruited with the promise of working on greenfield projects using the latest web frameworks, but the company’s direction had since changed due to an economic downturn and business refocusing. Peter’s boss had done his best to sugarcoat the new direction to the team, or so he thought, promising a return to the original plan “soon”, after every sprint.

Nevertheless, project after project for the past nine months clearly indicated that the former technology roadmap was out of the window, and the team started to notice.

Pete was angry, but this had nothing to do with the failed opportunity to learn Gatsby or Next.JS. He was angry that he’d been lied to, over and over again, just to be kept around.

As a leader of any team, you often need to balance two different sets of goals on a daily basis. On one hand, you need to deliver the work the team is supposed to do, and ensure it’s done well. On the other hand, and this is especially true for servant leaders, you need to enable your team to excel, helping each person to become their best version of themselves.

If you’re lucky, there’s enough alignment between these two camps, and your job is therefore pretty straightforward.

What’s more interesting is what happens in the other scenario, when there’s dissonance and conflict, as that’s really when your servant leadership skills are put to test.

Servant leadership and happiness

Photo by Priscilla Du Preez on Unsplash

Before we even get to managing this misalignment, let’s first take a quick detour to talk about the strange relationship that exists between servant leadership and happiness.

Often, the servant leader is depicted as a friend to the team members, while the traditional power leader is portrayed as a tyrant to be feared, or to hide away from. This is an overly polarized representation of these personas, as in the end they both need to satisfy the external goal we talked about earlier: delivering whatever work the team is required to do.

Unfortunately, that sometimes means making people temporarily unhappy, and that’s where we often struggle as servant leaders. In order to keep a positive mood in the team, we’re tempted to follow in Pete’s boss’ footsteps and, if not downright dish out white lies to the team, at least avoid communicating inconvenient truths. This slowly erodes the trust between us and the team, leading to resentment, which is the exact opposite of what we were trying to achieve.

To sum up, here’s what not to do: withhold important information from the team in order to keep them happy.

Instead, you’re better off applying empathy. Show the team how you’re also unhappy about the task / direction, while explaining why it’s so important to carry that out.

There’s no guarantee this approach resolves all negative feelings in the team, but at least it helps you project a trustworthy image, and it makes it more likely for a team member to share their feelings openly with you if they still harbor resentment.

As a leader, being a people-pleaser is less effective than being honest and trustworthy

Servant leadership and positivism

Photo by Allie Smith on Unsplash

Aside from empathy, there’s another key skill that can help you manage controversy in the team, and that’s positivism.

Positivism means spinning the information you present to the team to highlight the silver linings, or the positives, instead of just talking about the drawbacks of the work coming their way. Some people see this kind of spinning in a negative light as they associate it with the spin doctors who often help politicians massage their messages for the masses. That can’t be good, right?

Let’s do a quick exercise.

Imagine you want to convince a friend to join you in going to the gym. You’d probably highlight the health benefits of doing exercise, maybe going as far as saying how much fitter and healthier you feel since you started working out. You’d also most likely highlight the unique perks of your gym, such as its convenient location or the free juice bar you can hit after a cardio session.

If you want them to join you, you’re less likely to mention they’ll probably be sore for the first few times if they haven’t worked out in a while, or that the juice bar is often so busy that you’ve hardly been using it for the past few months.

Now, are you lying to your friend or are you just spinning the facts to make the proposition of joining you at the gym more attractive?

Most of us do this kind of spinning unconsciously or subconsciously when it concerns stuff we’re passionate about. The skill we need to learn as servant leaders is to find the silver lining for those things we dislike ourselves, and present all work to the team in the best possible light.

A servant leader can foster happiness by helping their team to see the bright side of any incoming task

Servant leadership and strategy

Photo by Randy Fath on Unsplash

Sometimes, no matter how good you are at spinning a particular task or project, certain team members might remain disillusioned. That’s OK, you can’t please everyone every time, and this is especially true when those tasks are in complete antithesis with a person’s career direction.

In these cases, again, honesty is your best friend. If the task is temporary, you can explain that to the person, and make them see how, realistically, their career won’t be affected too much by the detour. However, if the task is just an example of a permanent change in direction, it’s better to be upfront and let the person make the choice to either grow with the team, or pursue their goals elsewhere.

Is that too extreme?

It depends. On one hand, you don’t want to force a square peg in a round hole, or you’re going to damage both. On the other hand, innovation often comes exactly from this kind of outliers, the contrarians who rebel against the norms.

If you can, you should always try to create opportunities that are aligned with other longer term external goals, as secondary as they might be, before letting somebody go. For instance, for a software development team, that might mean exploring research topics that are outside the current feature set, but might eventually result in product innovation. Those topics may not be directly affect the bottom line today, but they might open up exciting possibilities in the longer term.

The team’s aspirations might be where the real innovation for your business lies

Wrapping up

Photo by Ian Schneider on Unsplash

Being a servant leader in times of trouble is tough. It’s all fun and games when the team’s internal goals are aligned with its external commitments, but proving times is where strong servant leaders really shine.

And here’s where the people-pleaser and the servant leader personas diverge. A people-pleaser always strives not to upset people, while a servant leader uses empathy to understand their team’s unhappiness and offer support through hard times.

In extreme cases, that means being able to identify that a person’s career growth might be better achieved elsewhere, and that’s cool. It’s better to make a person aware of the disconnect between their own goals and the team’s mission than to fabricate work just to keep them happy, or otherwise make empty promises in order to keep them on the team.

Having said that, a team isn’t a static construct, it’s an organism that evolves thanks to the aspirations and perspirations of its members, otherwise known as their career goals and their hard work. Before we accept somebody’s decision to depart, we should consider whether their aspirations can inform the longer term strategy of the team. Perhaps not all teams can afford setting up a moonshots subsection, but creativity and inventiveness are real assets for any successful business, and we should always strive to foster them whenever we see them budding.

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Omar Rabbolini
The Startup

Writing about life, technology, software engineering practice and startups | Website: https://drilbu.com