When you are the most senior person in the room, who tells you what you may be missing?
Being stretched isn’t the same as being busy.
You can have a relentless workload, carry significant responsibility and make difficult decisions every day, without encountering anything that genuinely challenges how you think.
Real stretch feels different. It tests your assumptions, exposes you to unfamiliar perspectives and asks you to work beyond what you already know.
Think back to a time when you experienced that.
What challenged you?
What did you learn about yourself?
How did it change the way you approached what came next?
And, importantly, how long ago was it?
Why can constructive challenge diminish as you become more senior?
As your experience and authority grow, people may become less inclined to question you.
Colleagues bring recommendations rather than unresolved problems. Information may be filtered before it reaches you. Your team becomes more capable, and familiar situations become easier to navigate.
These are often signs that you have led well. Yet they can also create distance from the challenge that once helped you develop.
In scientific and technical environments, considerable expertise can add another layer. People may hesitate to question someone with an established reputation, even when progress depends on sharing knowledge and testing ideas across different disciplines.
Without intending to, you can become surrounded by people who understand your thinking, respect your judgement, and rarely disrupt either.
What happens when senior leaders stop being challenged?
Experience brings valuable confidence, but it can also make familiar approaches feel unquestionably right.
Without enough constructive challenge:
Assumptions remain untested
Familiar perspectives dominate
Blind spots become harder to recognise
Feedback becomes more cautious
Learning and development begin to slow
Your team notices this too. If people see that agreement receives a warmer response than challenge, they quickly learn what is safest to offer.
This is also why the people around you matter. A strong network should include people who support you and people who are prepared to question you. Who is on your personal board?
How can senior leaders find the right kind of stretch?
You don’t necessarily need a bigger role or another demanding project. You may need to become more intentional about where challenge comes from.
Ask more specific questions
“What does everyone think?” rarely produces much challenge. Try asking:
What might I be overlooking?
What evidence points us in a different direction?
Where are my assumptions influencing this decision?
Who will experience this differently?
What would you recommend if this were your decision?
Widen the perspectives around you
Speak with people outside your immediate function, discipline or sector. Someone who understands the issue differently may notice possibilities that your usual network cannot see.
Create permission to disagree
Be explicit about wanting challenge, and pay attention to how you respond when it arrives. Curiosity encourages further honesty; defensiveness closes it down.
How you respond to challenge also shapes the quality of feedback people are willing to give you.
Learn from someone at a different career stage
A learning partnership with a more junior colleague can offer insight into changing expectations, technology and workplace experiences. It works best when both people can speak openly and learn from each other.
Choose something unfamiliar
A non-executive role, cross-sector project or new area of learning can place you in an environment where you are no longer the expert. The aim isn’t to add pressure, but to encounter different ideas and ways of working.
Create independent thinking space
Coaching offers a confidential place to examine your reasoning, test assumptions and explore the questions that colleaguemay find difficult to ask.
If you are considering coaching, Could you do with some thinking time? explores why having an independent person to think with can be particularly useful as responsibility increases.
The more senior you become, the less likely meaningful challenge is to arrive without invitation. Continuing to develop means actively seeking people and experiences that make you think again.
Who has permission to challenge you, and how readily do you listen when they do?
If you would value an independent perspective to challenge your thinking and consider how to develop your leadership and organisational impact, explore our Executive Coaching work or contact me to discuss what would help you.
Kate Jennings