Reflections on Leadership

At the end of every year, I write myself a letter recounting the year’s events. Some people may believe that writing to oneself in the third person is an early symptom of a latent split-personality disorder, but for me the activity reflects my belief that the “present Brendon” is a different person than the “past Brendon” or the “future Brendon”. The nature of these letters to date has been a passive examination of how things happened in the past, instead of a plan for what actions should be taken in the future. For this paper, submitted for one of my MBA organizational behaviour courses, I chose to use the “letter from/to myself” style to reflect on the elements of leadership that I need to incorporate into my life to enable future success:

Dear Brendon:

The next few years will be critical in determining whether you will evolve into a mature leader, confident in your abilities yet flexible in your interactions with others, or into an arrogant bastard, unable to reach your true potential. It’s not going to be an easy process to endure. It will test your sense of self-worth. It will require you to commit to continuously considering those around you. It will require you to put the needs of others ahead of your own needs. It will challenge you to think beyond the technical and quantitative world, to step outside of your “comfort zone”. It will require you to think strongly about what really matters in your life. In short: this is gonna hurt, but I’m only doing it because I care about you and your future success.

Think about some of the people you’ve looked up to as leaders in your short career: A and B. What were the qualities that made you respect them as leaders? A always made himself available, did more listening than talking, and was willing to trust the information provided by someone as junior as yourself during your time at IBM. B had similar characteristics – he was always able to see all sides of an issue, to focus on the positive and discount the negative, to discount his own knowledge of an issue to incorporate input from someone else, and to transcend personal conflicts in a discussion to focus everyone on moving things forward.

Working with A and B was enjoyable, primarily because you felt that your opinion on a subject was valuable to them. For work assignments, they told you what was going on, what they needed, and then they got out of your way. And when it came to talking about problems within the company, they never avoided the topic, always gave you the straight story and conveyed a vision of how things could be turned around. This behavior translated into the desire to meet or exceed their expectations – you felt connected to them and the goals they defined. This connection translated into greater motivation, and the desire to “stretch” your capabilities and grow in the manner required to meet their lofty goals.

A lot of A and B’s power came not from their position in the company, but from their ability to involve people in what they wanted to achieve. They were persuasive enough that they could have convinced you to donate your socks to them. And then get you to purchase the socks back from them.

That’s not too say that A and B were ideal – no one’s ideal. In some cases, they could be too conciliatory, too willing to listen endlessly, to not make a decision. If there was one thing that they could have done better, it would have been to take a little more aggressive stance with respect to making decisions. That aside, their positive points far outweighed their negative points – they always seemed open to changing themselves as required to address any personal shortcomings.

Now, contrast the styles of A and B with those of C and D, possibly the worst managers/best non-leaders you’ve ever experienced. C was the “invisible manager”, never available to answer questions or provide feedback, always expecting you to perform tasks without ever describing a specific project. D, on the other hand, was a micromanager who didn’t accept the opinions of his team, including those eminently more qualified than him, and derided other members of the team in private conversation.

Remember how de-motivating it was to work under those guys? You didn’t know what you were supposed to be working on half the time because they didn’t tell you, or didn’t really seem to know themselves what you were supposed to be working on. If you did something the way you thought was correct, you only ended up having to re-do it when C finally got around to telling you want he actually wanted, or when D dropped by to give you a “step by step” method for solving the problem “as he saw it”. You had little opportunity to make a contribution to the company that you viewed as meaningful.

In many cases, there was simply no consistent, cohesive communication of project goals and direction by either C or D. This management style translated into frustration, self doubt, tension, and infighting within the development team. All of these characteristics resulted in glacially slow project progress, which further fed the frustration, self doubt, tension and infighting in a vicious cycle. Deadlines came and went without much progress. Even confronting the leadership issue did little, as both C and D were blind to the effect their actions and words had on members of the team or the team morale.

No wonder you left both of those jobs!

C and D differed from A and B in one very specific fashion: they were always prepared to make a decision. In fact, they probably only talked to you to inform you of the decision they had already made without your input. This style made for faster decision turnaround in the short term, but ironically led to protracted emotional debate within the team on the proclaimed decision that took longer than it would have taken to make a decision in concert with the team. Quick decision making is a good trait, but unfortunately C and D practiced quick decision making in isolation, neutralizing the benefit of this trait.

So, which kind of manager do you want to be: an “A and B”, or a “C and D”? As you’ve already seen in the companies you’ve been a part of, the success of a technology company has little to do with technology. In any company, success is the result of your ability to lead, to manage human resources – the creation of a new technology or product just happens to be the saleable end result, a side-effect, if you will. And if you want to run a successful startup, you’re going to have to master the ability to harness and enrich the capabilities of your team.

Perhaps that what scares you most: the fact that you can see elements of C and D in your own personality, and you’re not sure you’ll be able to “drop the tools” you’ve used to date when you need to find another way of getting things done. You’re scared you’re going to turn in the “asshole boss” and not even know it until it’s too late. Then again, the fact that you’re even concerned about these issues is a good sign that you will be able to avoid that fate- you’d be far worse off if you weren’t even considering these aspects of personal development. The key will be to identify what aspects require improvement, or are essential to becoming a leader like A or B.

To become an A or a B, your will have to overcome your greatest shortcoming: your inability to listen openly to those around you. Though you always have something to say on any given topic, your tendency to provide any and all information at your disposal usually precludes others around you from volunteering any information: “Brendon already knows the answer or soon will, so why bother speaking up?”

In a leadership position it will no longer necessarily be your job to come up with solutions. That’s not to say your job won’t require you to provide direction, a vision, to guide the team. However, how you communicate this information will be just as, if not more, important than the information itself. It will be your responsibility to harness the expertise of your team and guide them to come up with solutions. To do this, you will need to act more like a receiver and less like a transmitter of information to provide those around you with the opportunity to prove themselves, to communicate their viewpoint, to “stretch” their abilities, and feel that they’re making a valuable contribution to the team. After all, if you already know all the answers, why do you need a team in the first place?

A source of potential “C and D”-ness will be your current belief that when you have the ‘authority’ to take charge, you’ll be able to force teams to work. Remember: C and D had the authority, but they still couldn’t force things to work. Though authority bestowed by your position as a manager may be useful as a last resort when all else has failed, it won’t help you the majority of the time. Instead, you’ll need to change your attitude, adopt new tools to use when interacting with people that will serve you better than your position within the corporate hierarchy.

Part of this change will require you to put aside your engineering training, specifically the engineering focus on definable, quantitative solutions. In engineering, there is always a right answer and a wrong answer – and it’s your job as an engineer to discover the correct answer. But leading people will require you to be less “hands-on”; though you may be able to get certain tasks done faster or “better” than your subordinates, you will need to resist the urge to take on these tasks. Only by allowing your team to do their job will they have the confidence and motivation to succeed at some point in the future when their ability to perform really matters. You will also need to accept the fact that the answers or solutions required build a team will not be as black-and-white as the solutions to engineering problems.

Your adherence to the engineering requirement for “perfect” solutions will also need to be toned down. In the “shades of grey” world of interpersonal relationship and team leading, there are no perfect answers. You will need to be satisfied with the output that gets the job done, and shift your efforts to enabling people to achieve steady, perpetual improvement.

A final aspect of your engineering training you will need to tone down is your critical nature. The engineering discipline requires its disciples to dedicate themselves to finding problems where none appear to exist to a layman’s eyes. Though an admirable quality when a technical oversight can cost lives, this skill tends to focus on the negative (“what isn’t working?”) as opposed to the positive (“what can we do to make it work better?”). Your job as a leader will be not to dwell on the past failures, but focus on the possibilities of future success. Saying it can’t be done will only convince your team members that it can’t be done, so why try? In the words of your mother: “accentuate the positive!”

On that note, let’s stop considering your leadership shortcomings and focus on the positive! Let’s consider your current leadership strengths.

There, done. That was easy, wasn’t it?

Just kidding. See? Self-deprecating humor, that’s a leadership strength you possess. It will serve you well when a tense situation between team members, or a team member and yourself needs to be diffused without either party losing face. Though humor can provide the momentary tension relief, you will need to choose the appropriate time to use this technique – choosing the wrong moment or misjudging how humor might be received by other parties could be disastrous. Not only could it be unwelcome to the situation, but it also could be considered derogatory or disrespectful. Use this power for good, not evil.

Your ability to come to a decision quickly will be another skill that will help you lead. One quagmire you’ve seen in your experience has been the lack of a “decision to make a decision” – usually due to a manager that either doesn’t want to take responsibility for charting a course for the team or that is afraid of wounding the pride of any member of a team who has expressed an opposing view on the correct course of action. Again, you will need to choose the appropriate time to come to a decision – too soon could squelch valuable discussion or ideas. Too late could equally have negative ramifications due to the delay to adopt a course of action. The challenge will be to strike a balance between the two, or choose the right time to pre-empt discussion when time is of the essence.

A final skill that will enable you to lead will be your tendency to “think big” and rally against accepted norms. All of your heroes thought big – and it’s only through dreaming of “what could be” and effectively communicating that dream to others that you will be able to achieve similar outcomes. People need to believe in something, and your passion and imagination will inspire people to do more than they or others think possible. In the end, “thinking big” and being unafraid to take a chance by thinking outside the box will make the difference between a dream and reality. In the end, using this skill with good intentions and accepting the risk that comes with its use will be the essential skill to becoming a leader. After all, as Peter says, “if it’s not risky, it’s not leadership!”

The final message I would leave you with to guide your future personal development as a leader: be prepared to grow and change. Though you’ve got an early start on a number of critical leadership skills, you will always need to learn more and adapt to different situations. Different people will require different approaches and have different personal preferences as to how they interact with others. To truly be a leader, you will need to overcome you sensitivity to criticism of your capabilities and accept the feedback on your leadership without becoming defensive. If you can achieve that, the rest will be easy.

So, until we see each other again: go out and become a leader. Good luck!

Your former self,

Brendon J. Wilson