The One Challenge All Leaders Secretly Face

For the last few weeks I’ve been working with a client who has provided an interesting opportunity to examine one of the challenges leaders find themselves struggling with in today’s fast-paced business world. Tom* serves as one of the senior department heads at a mid-size technology firm, overseeing the development and marketing of some of his company’s key product lines.

On all accounts, Tom has consistently demonstrated the key traits of being an effective leader, as evidenced both in his performance reviews as well as in his team’s track record of successful product releases. However, on the heels of some rather lukewarm responses from both the market and industry critics to their latest efforts, Tom has been grappling with uncertainties over his ability to continue leading his team in the months ahead.

Although these recent developments haven’t lead to any negative reactions from senior management, Tom has nonetheless been feeling like he was thrown off the proverbial horse, despite the fact that his team remains determined to keep building on their past successes. The current situation has stirred up feelings of self-doubt in Tom; about whether he would be able to continue to successfully lead his team or even if he was still the right person for the job.

Through the course of our coaching sessions, we came up with a number of strategies Tom could use to help him overcome these feelings of self-doubt so he can continue to support his team as they push ahead.

Of course, Tom is not alone in feeling at times this sense of uncertainty over one’s ability to successfully lead those under their care.  With this in mind, here are some measures that can help others in leadership positions regain their footing onto more certain ground as they navigate their organization through this constantly-changing business environment.

1. Offer help to those around you
No matter what your position is in your organization, all of us are driven by a need to know that we can be of help, that what we do matters to those around us. For leaders, these moments of self-doubt are a perfect opportunity to get out from behind the desk and wander around to see what your team is up to and how you can help them complete some of the tasks currently on their plate.

Your impromptu lending of a helping hand will not only remind your team of your role to help them succeed, but it will also give you that feeling of accomplishment you need to get past these feelings of uncertainty over your ability to contribute in a meaningful fashion.

2. Seek out opportunities to learn new ideas and approaches
Sometimes our sense of uncertainty about our abilities is less a result of some failure as it is a manifestation of this feeling that we’re stuck in a rut, where we’re no longer growing but simply going through the motions. One obvious way to get past this is to take active measures to build on your existing skills/abilities by taking courses, reading books, or soliciting the help of a coach to help you discover new opportunities within your current position where you can grow and learn.

Making the effort to learn more about the process of leading your team will not only help open your mind to new ideas or approaches, but it will also help you grow as a leader.

3. Start building a “Rainy-day gratitude bank”
If you’ve been doing a good job serving as a leader in your organization, you’ve probably received many emails or notes of gratitude, both from your team as well as from your customers, expressing their appreciation for your leadership and guidance. When things are going well, these little gestures help to reinforce your perception that you’re playing at the top of your game.

But instead of simply tossing these messages aside and moving on, collect all of them and create for yourself a “Rainy-day gratitude bank” – essentially a folder where you can keep track of these messages and gestures which help to underscore your past successes. When you’re finding yourself questioning your ability to lead, take this folder out and review what was said about your leadership as a way to remind yourself of what you’re capable of and how you are able to direct your team towards reaching your shared objectives.

Having that outside perspective is important to making sure you not only stay on track, but continue to perform in a manner which creates the desired results you want from your team.

4. Manage your own expectations
One of the responsibilities of being a leader is creating a vision of what you’d like your organization to accomplish, both to help define what you expect from your team as well as to clarify the direction you’d like your organization to take.

But how many leaders also take the time to develop a vision of what they expect of themselves? Unfortunately, this step is often overlooked and consequently, it ends up being defined by outside factors. As such, it’s no surprise that many leaders soon find themselves struggling with self-doubt as they lack any real guideposts to help them stay the course.

So if you haven’t already done so, create a list of realistic expectations you have for yourself and store it for easy reference. Being able to refer to this list will help you ensure that you’re not only staying on target, but that you’re living up to your own expectations. Remember, it’s hard to manage others if you’re not able to manage yourself first.

When a leader helps their team achieve their goals or reach many success markers, it’s easy to fall into that misguided presumption that you’ve figured out how to be a good leader and can simply coast along on those behaviours or tactics. However, to be truly effective in the role of leadership requires continual learning and development so that you can remain in service to your team as they develop and evolve.

At the end of the day, it’s also important to recognize that we all suffer from those moments of uncertainty, sometimes brought on by a very public failure, other times as a result of our own natural insecurities regarding our abilities as our organization continues to evolve and grow. Allowing ourselves to be open about these doubts and taking positive action to not only address them, but manage them, will help you pass through them quicker so you can dust yourself off and get back on the horse.

*Name changed.

4 comments on “The One Challenge All Leaders Secretly Face

  1. Tanveer, I think you are providing some good solutions here. Especially point #2. I think all good leaders in good times or tough times need continually learn new ideas or approaches. I think it has become easier with the advent of social media, because if one goes online on regular basis follows or connects with the right people they will learn – stay informed.

    However, candidly Tom does not sound very confident given the level of success he has achieved. Therefore I suggest he learn from the wisdom of Frank Gehry, famous architect: When artists/creative people step outside the norm they must accept criticism, wear it like an article of clothing for a while, then toss it and move on. Tom should focus on what got him to the party.

    1. Thanks Jim; it's been nice to see how these different solutions resonate with people. In my coaching sessions with Tom, we've been working on how he can use these and other solutions more applicable to his situation to help him address his feelings of self-doubt.

      And speaking of Tom, you're absolutely right that he was suffering from a lack of self-confidence, something that became more apparent to him as we delved into this. What helped was getting him to recognize that his feelings of self-worth, of how he felt about his own compentencies, really hadn't changed. Instead, what was affecting him was this external pressure he was putting on himself due to his own perceptions that he was no longer successful.

      This helped him to appreciate that while our self-confidence understandably takes a hit every now and then thanks to conditions that are outside of our control, if we focus on what we can control – namely our internal belief in ourselves – the hits one takes to your sense of self-confidence won't be as impactful on your perception of your ability to lead your team.

      As Henry Ford said "Whether you think that you can, or that you can't, you are usually right."

      Thanks again for your comment, Jim. Always enjoy the thoughts they help spur on.

  2. Tanveer, Tom might be assured to know what I've discovered over many years of working with CEOs, Boards of DIrectors, and other top leaders.

    Many of them periodically look out their huge office windows and pray to God that no one finds out they don't know what they're doing. (now it's an exaggeration of course, but the fear is of "being found out." And these are very successful Executives!

    I'll add to your collection of quotes on the matter: "You don't know you're the lead dog unless you have bites on your ass." (I'd edit the word but buttocks didn't do the feeling justice.) a business partner of mine attributed to her grandmother.

    and …"Courage is resistance to fear, mastery of fear, not absence of fear. Except a creature be part coward, it is not a compliment to say it is brave."
    ~ Mark Twain

    and … "you can't push the envelop and be confident at the same time." me

    and "if you're confident, you're setting your sights too low." also me 🙂

    1. Thanks for those quotes, Chris. I think it’s important that we recognize that it’s only natural for leaders to have these moments of doubt and uncertainty. After all, unlike those they lead, leaders can’t exactly walk up to another employee and openly express hesitation about their abilities or their efforts as it’s a sure way to undermine the trust they need in those under their care. However, by taking that first step of acknowledging and embracing this reality, it’s easier to find that outside support all leaders need to help them properly gauge their efforts. Taking stock of their past accomplishments will also help them to build up their level of self-esteem so that when those moments of doubt occur – as they will – it won’t be as deleterious or damaging to their perception of their leaders.

      Thanks again, Chris, for sharing your thoughts on this piece.

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