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Insecure Overachievers



A desire to be overly self-critical.


It would surprise you how often I hear these emotions and sentiments raised by the executives I work with. These are people who have "made it" in society's eyes or are on track to do so. They have zoomed past many career milestones and achieved incredible things. And are on the way to continuing doing so.

Let me introduce you to the Insecure Overachievers.

Insecure overachievers and the above-and-beyond business model that perhaps fuels their growth have become pervasive. This is true more so today than ever before.

"Insecure overachievers are exceptionally capable and fiercely ambitious, but driven by a sense of their own inadequacy."

I am inspired by my clients and what they achieve in their careers and work. My work with two recent clients has galvanised me to put pen to paper on this topic. Too few people within elite professional and financial services are prepared to do so because they have no economic incentive to do so. Why rock the status quo?

My clients are both very senior, highly successful women who work in financial and professional services. Both have made it to the most senior levels of their profession. Something they each have been working towards for many years. To an outsider, even the insiders, they have everything: the title, the office, the power.

They have a seat at the table. Yet often wonder, "What is it exactly that I bring to the table?"

They keep stepping up and making it happen.

And yet elevated anxiety levels are the norm for insecure overachievers. Anxiety often driven by their irrational worries that their work may not be good enough or that they have not done enough. Factors like these negatively impact physical and mental health, family and friends, and eventually, the work itself.

From my coaching work with executives over the past five years and my prior career in elite financial services, I see several contributing and compounding factors.

Let's delve in…

Above and Beyond Business Models

Many companies have built their business model on their people constantly going "above and beyond" their job descriptions. This situation isn't unique to elite professional and financial services firms, where rapid promotion and steep increases in monetary compensation are the rewards for doing more than one's peers. For example, I recently reviewed the job description for a client's new role, which was for a sector far removed from what one would typically perceive as fast-paced. The job description contained twenty primary responsibilities, individually detailed. And at the end of the list, it said:

" when required, during evenings and weekends, undertaking duties as required."

and finishing with

"The above list is not exhaustive."


Is it any wonder that the insecure overachiever is fundamental to the success of a business model that relies upon knowledge workers having a dysfunctional relationship with work? This model is well suited to someone who doesn't have a very good sense of self and struggles with maintaining robust boundaries between work and non-work.

Firms with an above-and-beyond business model create the ideal environment to exploit these insecure overachievers by combining internal competition with a lack of transparency.

Lack of transparency

The antidote to a lack of transparency is:

Inner transparency - do you see yourself clearly? An inward self-awareness, what drives us, what we prefer, and what patterns or people trigger reactions in us.

External transparency - do you know how other people see you? If we can see ourselves from another's point of view, we will likely be able to change our behaviours, avoid unnecessary conflict and build stronger relationships.

Yet a robust culture of feedback is routinely lacking in many (many) organisations, even though feedback is a powerful way to improve performance at almost anything. A common theme affecting the executives I work with is a lack of actionable feedback from those around them. The annual performance appraisal system that is supposed to be a source of valuable, insightful 360 feedback is often a tick-the-box, "sheep dip" exercise. Only occasionally will a manager have the time and care deeply enough to produce constructive, actionable insights rather than the generic, nondescript feedback that employees feel safe to enter into the black box system. Is it any wonder that articles in The Harvard Business Review routinely refer to research that shows things such as: "Two-thirds of managers are afraid of telling their direct reports hard feedback for fear of how they'll react"?

The insecure overachiever compensates and must resort to mind-reading because of the lack of transparency, which can lead to unnecessary anxiety, self-doubt and being overly self-critical.

Psychometrics such as Hogan Assessments, which I use in my coaching, provide a unique insight into the depths of personality and cognitive reasoning. Combined with coaching, the Hogan tool will help performance, organisational fit and leadership effectiveness by strengthening our inner transparency.

Feedback is the best way to obtain external transparency. One of my clients described the insights they received from the feedback he received as part of his coaching as "particularly valuable as they helped me realise the gulf between how I thought I was perceived and how I actually was perceived. This formed the basis of a series of constructive changes over many months."

Who wouldn't want this transparency and increased self-awareness? Clarity helps us to identify things to start doing, stop doing or improve. And yet,

"Nobody has ever told me that before."

"This is the first time I have heard that."

Are comments I hear from the people that I work with - further evidence of cultures where feedback is lacking.

Is it any wonder that with the above-and-beyond business model, along with the lack of robust feedback, people end up continuously raising the bar again and again, which leads us full circle to perfectionism?

Done is better than Perfect.

Wabi-sabi is a Japanese philosophy often described as appreciating the beauty in imperfection. Wabi-sabi in daily working life requires a shift in perspective from one that chases perfection to one that appreciates what is.

There is no such thing as a perfect leader. There is no such state, whatever articles in Forbes or Time Magazine and social media that put leaders on public pedestals lead us to believe.

Perfect isn't the point. The key is to focus on continuous learning and developing yourself and your team. Improve your strengths and work on imperfections, but don't expect them to disappear entirely. And that is ok.

My advice to overachievers is to recognise what triggers their insecurity, to start to define success in their own terms - not only those of their employer - to trust the evidence of their career success and begin to enjoy what this brings. Coaching can help, initially, by creating awareness by exploring how you come across to others and how you view yourself. Over time, coaching can help strengthen your psychological capital: self-efficacy, appreciation for the present and optimism for the future, as well as develop new habits to build resilience and change your relationship with work.

The insecurity that drives the insecure overachiever may diminish with continued success, but it never goes away, so it is essential to make peace with it - or play a different game altogether.

🏋️ Challenge: Start to build a personal feedback loop

Stop being a mind reader. Stop using the force and assuming you have Jedi powers to read the minds of people you work with. Start to ask for feedback and become a role model who is proactively seeking feedback and constructively acting upon it. Here are nine steps to building a supportive, challenging, and positive feedback loop. See how many you can action in the coming weeks and which ones work for you, so you can build enduring new habits:

  1. Proactively ask your current boss. Specificity is essential. Don't just ask, "How am I doing?" What could you be doing more of, starting to do, or stop doing to be more helpful/impactful in the team? Look to help solve their problems and link the feedback to the issues they may be facing.

  2. Ask a previous boss. Ask specific questions such as "What did I do that used to drive you up the wall or that caused you to cover for me or put out fires that I inadvertently caused and was unaware of?"

  3. Find a mentor at work who will observe you in action and provide timely and constructive criticism.

  4. Ask a friend either at work or someone you know outside of work - again, be specific. Generic questions aren't beneficial.

  5. Ask a trusted peer to provide specific feedback - have them watch you in a meeting or when you are speaking.

  6. Listen carefully to what people are really saying. Pay attention to what people are saying, what they aren't saying and how they say it.

  7. Watch successful people in action - what do they do that makes them so successful, and how is it different to what you do? How might you authentically develop that skill or behaviour?

  8. Get an independent executive coach - a coach is a trusted, independent partner. Someone who will hold you accountable and provide an outside perspective to help you see yourself as others see you.

  9. Form a challenge group. Unlike a support group, they will challenge your logic, identify holes, and improve your reasoning and thinking to develop more compelling solutions.

It takes a great deal of self-reflection and the courage to hold the mirror up to one's face and take a good look.

To proactively and regularly seek feedback and act upon it.

But leadership isn't about taking the easy option.

It is about doing the small things that make a difference and improve life at work.


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