In this edition of Insights into Leadership, I share the anonymised story of a senior leader whose confidence had fallen despite years of evidence that she was highly capable. I explore what sat underneath that loss of confidence, how reconnecting with her achievements and strengths helped rebuild self-trust, and why redefining success became an important part of deciding what came next.
By the time one of my clients came to coaching, she had already built what most people would regard as a highly successful career. She had spent many years progressing within the same organisation, reached a senior People leadership role and developed a strong reputation for delivering complex organisational change.
There was no obvious question about her capability. She had experience, credibility and a track record of delivering at a senior level. Yet, by the time she decided to leave the organisation, the way she felt about herself bore very little resemblance to the evidence of what she had achieved.
She resigned without another role to go to and began coaching while recovering from burnout. Her confidence was low, she was uncertain about what she wanted next, and she found herself caught between two competing thoughts. One part of her wanted to continue progressing into a more strategic and influential leadership role, while another part questioned whether she was capable of doing so.
This tension between ambition and self-doubt is something I see regularly in experienced leaders. They may still be performing well and have years of evidence that demonstrates their capability, yet privately they are questioning themselves in ways they never used to.
At first, the questions my client was asking were understandably focused on what came next.
• What role should she look for?
• What level should she be aiming at?
• How should she position herself in the market?
• What should the next stage of her career look like?
They were all legitimate questions, but they were not the questions we needed to answer first.
One of the things that became apparent early in our work together was that she didn’t simply need a job-search strategy. She needed to reconnect with her own sense of value.
Years of achievement had not protected her confidence. Despite everything she had accomplished, she had reached a point where she could explain what she had done professionally far more easily than she could recognise what those achievements said about her as a leader.
That distinction matters because we often assume confidence is the natural result of achievement. We believe that if we progress, deliver difficult work, receive positive feedback and accumulate enough evidence of success, confidence will inevitably follow.
In practice, it doesn’t always work that way.
A leader can have a considerable amount of evidence that they are capable and still struggle to believe it. They can be trusted by the people around them while privately questioning their own judgement, and they can reach a point where another achievement, promotion or piece of positive feedback is no longer enough to change how they feel.
Much of our early work therefore involved looking back before deciding what should happen next. We explored the significant moments, challenges and achievements across her career, not to dwell on the past but to help her see it more accurately. We began to identify the organisational impact she had made, the difficult situations she had navigated and the contribution she had made as a leader.
Over time, this started to change the story she was telling herself. Instead of automatically minimising what she had done, she began recognising the leadership capability underneath those achievements: her ability to influence, deliver, make decisions, navigate complexity and lead others through change.
This was not about manufacturing confidence or trying to persuade her to think positively. It was about reconnecting her with evidence she had stopped allowing herself to see.
When confidence falls, the internal narrative can become remarkably persuasive. Decisions that once felt instinctive can suddenly require far more thought. Attention shifts towards what you don’t know rather than everything you do, and setbacks can begin to feel like confirmation of your doubts rather than a normal part of making a change.
For my client, being between roles added another layer of uncertainty. She had spent most of her career in continuous employment, so suddenly having no job title, organisation or daily structure was unfamiliar. Rejection during the job search became difficult not because she lacked resilience, but because it landed at a point when her confidence was already fragile.
We therefore focused on creating a sense of progress that didn’t depend on somebody offering her a job. She began to challenge some of the negative assumptions she was making about herself, recognise smaller achievements, create realistic daily goals and rebuild routines that gave her a greater sense of momentum.
We also spent time understanding her energy. Rather than thinking only about which role she could secure next, we explored the environments in which she performed at her best, the work that gave her energy, the situations that depleted it and the conditions she needed in order to sustain her performance over the longer term.
This gradually changed the nature of the career conversation. Instead of simply asking which job she should take, she began asking what kind of working life she actually wanted to create.
That is a very different question.
One of the most important shifts came when my client began to question the criteria she had historically used to define career success.
Like many experienced professionals, progression had long been associated with greater responsibility, a more senior title and increased salary. Those markers had played an important part in her career and there was nothing inherently wrong with wanting them. The question was whether they still represented what mattered most to her now.
As our coaching progressed, she recognised that other things had become more important. Time with her family, balance, organisational culture, meaningful work and the ability to operate in a way that aligned with her values had moved much further up the list.
This sounds straightforward when written down, but it can be surprisingly difficult to acknowledge when you have spent decades building a successful career. Professional identity can become deeply connected to progression, responsibility and status, which means questioning whether you still want the next step can feel uncomfortable. For some leaders, it can even feel as though they are becoming less ambitious.
That was not what was happening here.
My client was not lowering her expectations or stepping away from her potential. She was becoming more discerning about where and how she wanted to use it.
She became clearer about the strengths she wanted to bring to her next role, the organisational environments in which she could thrive and the things she was no longer prepared to compromise. Most importantly, she began approaching her next career decision from a position of greater choice rather than feeling that she had something to prove.
At the end of our six coaching sessions, my client had not yet secured her next role, and I think that is an important part of this story.
It would make a neater case study if the outcome were a significant promotion, an impressive new title or a substantial increase in salary. Yet focusing only on those outcomes would overlook the more fundamental change that had taken place.
She described herself as being at a turning point. She felt more grounded, more self-aware and increasingly able to recognise her achievements without immediately dismissing them. Her confidence and self-belief had begun to return because she was reconnecting with the value she already brought rather than waiting for somebody else to validate it.
In her words:
“The biggest shift has been in my confidence and self-belief. I’ve gone from questioning my worth to recognising the value I bring as a leader.”
She was also much clearer about what she wanted from the next stage of her career and life. Success was no longer defined solely by finding the most senior role available or achieving the highest salary possible. It was about finding work that allowed her to contribute at the level she knew she was capable of while still creating the life she wanted outside work.
That clarity changes the way you approach career decisions.
• Instead of focusing entirely on whether an organisation wants you, you begin to consider whether you want what it is offering.
• Rather than asking whether you are good enough for a role, you can ask whether the role enables you to use your strengths.
• Instead of following assumptions about what someone at your level should do next, you can decide what matters to you at this stage of your career.
Although this is one leader’s experience, the underlying pattern is one I recognise in many experienced senior leaders.
They have not suddenly become less capable, nor have their years of experience disappeared. Their judgement, knowledge and leadership ability are still there. What has often changed is their connection to those things.
Years of sustained responsibility, organisational pressure, difficult experiences, constant adaptation and prioritising the needs of the business can gradually alter the way a leader sees themselves.
• They continue to perform but increasingly question how well they are doing it.
• They continue to make decisions but trust those decisions less.
• They remain the person others rely on while privately wondering whether they are still as capable as everyone seems to believe.
It can look like a confidence problem, but sometimes confidence is only the visible symptom.
Underneath it may be a loss of connection to your strengths, a habit of discounting your achievements, a definition of success you have outgrown or a working life that no longer reflects what matters to you. It may also be the result of spending so long responding to the expectations of other people that you have stopped asking what you want for yourself.
That is why I don’t believe the answer is simply to teach experienced leaders how to appear more confident.
The more important work is often rebuilding the self-trust underneath it. It’s about recognising what you already bring, understanding what has changed, deciding what matters now and learning to make decisions from that place rather than from exhaustion, fear or the need to keep proving yourself.
My client described coaching as giving her the space to pause, reflect and properly consider what she wanted from the next stage of both her career and her life.
That pause was important because moving forward doesn’t always begin by asking what you should do next.
Sometimes it begins by understanding who you are now, recognising the value that has been there all along and learning to trust yourself again.
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