False Starts at the Top -Are they Avoidable?

– Yoshita Swarup Sharma

Dear Leader,

Have you ever stepped into a bigger role… and felt the ground shift under your feet?

I am not referring to a seismic earthquake, but more of a wobble, that makes you less sure of your footing.

In the last few years , my LinkedIn DMs have been filled with messages from senior leaders in exactly that place.

Brilliant, capable people, quietly admitting:

“I thought I’d be running from Day 1… but instead, I’m struggling.”

And as a leader, false starts can be brutally hard to recover from.

The DM Stories That Stopped Me in My Tracks

Here are a few absolutely real examples of what I have heard through my Linkedin connects (anonymised, of course)

• A leader joins a top notch multinational consumer-goods company in a newly carved out role with big dreams. 30 days in, there’s still no org-wide announcement. No one knows who they are or why they are here.
• Another walks into a promising startup role wanting to make big impact, but finds themselves boxed in by a toxic working relationship.
• A third takes a big leap to another part of the organization and immediately feels swamped amidst a hostile vibe.
• A fourth celebrates a promotion, only to be “demoted” after six months when a new layer is added above them.

To my surprise and disbelief, I could see many senior leaders moving to bigger roles feeling unsupported, judged and somewhat lost on the inside. Of course, they did not feel safe enough to share this with their organizations.

They wore masks that showed that they had things under control. Some of them were afraid that they would be seen as incompetent.

But, on closer observation, these weren’t stories of incompetence. These were stories of isolation, self-doubt, and quietly eroding confidence.

These were also stories of transition.

If this has been your experience too, you are not alone.

Why Transitions Trip Up Even the Best Leaders

Role transitions are hard.

Wanting a promotion every 2 to 3 years is one thing -successfully navigating into a bigger role (whether in your current organization or a new one) is another entirely.

Many leaders look at it as “make or break” because they are under scrutiny.

They put themselves under so much pressure. But, honestly, it is a bit of a tightrope walk at that level. Several challenges can crop up.

The Seven Transition Challenges I See Again and Again

Once the euphoria of the big move settles, leaders look around and find a gap between what they expected and what actually is.

That can feel unsettling.

A leader who had been hired to turnaround a business told me this:

“They did tell me that things were bad and I had to turn them around, but they did not tell me it was this bad!”

Joining the dots on thousands of leader and stakeholder conversations we have done at A Brighter Life , here are the most common challenges we see when coaching leaders in high-stakes transitions:

• Feeling unsure about who you are in the new role: As expectations change, even seasoned leaders can sense that they are expected to show up differently.
• Underestimating the culture gap: Every organisation has its unspoken rules – how influence is built, how conflicts are handled, how quickly things move. It can be disorienting.
• Misreading power and influence: On paper, org charts show formal authority. In practice, influence is nuanced. Who vibes with who, whose voice matters- this gets uncovered slowly.
• Rushing to prove yourself : The pressure can tempt leaders into quick fixes without fully understanding the problem. Enthusiasm and 90 day narratives can be quite treacherous.
• Leading a team you didn’t choose: Inheriting a team means inheriting its history – loyalties, frustrations, strengths, and blind spots. Leaders have their agendas, but it is the team that has to deliver.
• Gauging executive presence in the new context: Multinational companies, Indian conglomerates, Family run businesses, Tech startups – all have different boardroom etiquettes.
• Holding onto past solutions instead of unlearning: Success in your previous role often comes from patterns you’ve mastered – but those same patterns can hold you back if the new environment requires a different approach.

That’s a lot to cover, isn’t it?

The Need Gap No One Talks About

It is counter-intuitive that organizations frequently hire or promote leaders into high-stakes roles and then leave them to “figure it out.”

One Talent Head told me:

“We have a 90-day wait-and-watch approach. We’re paying top dollar for top talent; they’re expected to deliver.”

In 90 days! Really? Isn’t that a bit unrealistic?

Here’s my inner chatter.

“The leader is human. The change is humongous. The expectation is high. Leaders don’t have a magic wand for this new context! They will evolve and transform, of course. But it’s a process. They need support!”

You tell me. If you were investing heavily in something, would you not do everything possible to ensure its success?

Yes, of course. But what?

Why We Created The Leadership Transition Lab

That is why, in spite of doing transition focused executive coaching for many years, Ashwni Sharma, PCC- ICF, MGSCC and I felt that there was a need to take transitioning leaders through a more structured lab to set them up for success.

Our newly launched offering, Leadership Transition Lab (LTL) offers a high-trust, practical 1:1 space over 6 months for newly hired and promoted leaders to understand expectations, anticipate landmines, discuss options and settle into their role with more clarity and confidence.

No judgments. Just the right conversations at the right time. In confidence.

You can read more about the program here.

💡 Leadership Mirror:

For now, here’s a quick question I would like to leave you with:

If you were stepping into a bigger role tomorrow, how would you support yourself through the transformational journey it would undoubtedly be?

In the coming editions of CXOJourneys, we’ll be diving deeper into this.

Each month, we’ll explore the untold stories, and key themes of leadership transitions—the messy parts no one talks about. And I will share with you what I have seen working. Or not.

If you believe these insights could be valuable for your journey, I invite you to hit subscribe and follow along.

I have finally bit the bullet on LinkedIn newsletters! Do let me know what resonated and what you would like me to share. I would love to hear from you.

Until next month,

Joy & Abundance,

Yoshita Swarup Sharma

Facilitating Transformative Leadership Transitions for CXOs and Senior Leaders; Co-Founder, A Brighter Life

FAQs 

1. Why do experienced leaders struggle when transitioning into bigger roles?

Even seasoned leaders can falter because new mandates often demand different mindsets, cultural understanding, and influence dynamics. The pressure to prove oneself quickly, without structured transition support, leads to early missteps.

2. What are the most common challenges faced during senior leadership transitions?

Key struggles include culture gaps, unclear role expectations, misreading informal power structures, and rushing to deliver results before building alignment or trust. These “false starts” can erode confidence early in a new role.

3. How can executive coaching help prevent false starts in leadership transitions?

Executive coaching creates a confidential space for reflection, strategic alignment, and mindset recalibration. Programs like A Brighter Life’s Leadership Transition Lab help leaders anticipate landmines and build clarity during the first 180 days.

4. Why do organizations underestimate the need for leadership transition support?

Many companies assume top talent will adapt naturally, but fail to recognize that new contexts require new behaviors. Without structured coaching or stakeholder alignment, even high-potential leaders can struggle to integrate effectively.

5. What is the Leadership Transition Lab and how does it support newly promoted or hired CXOs?

The Leadership Transition Lab by A Brighter Life is a six-month, one-on-one executive coaching journey designed to help CXOs and senior leaders navigate new mandates confidently, align with stakeholders, and succeed from day one.

Yoshita Swarup Sharma

Founder & CEO – A Brighter Life | ICF Certified Executive Coach  | Leadership facilitator | NLP Practitioner| Inner Transformation Specialist

“What the caterpillar calls the end of the world, the Master calls a butterfly” Yoshita lives life by the famous lines of Richard Bach. She is a management graduate from Symbiosis Institute of Business Management and economics graduate From Hansraj College, Delhi University. She has been an accomplished marketing professional before embarking on a second career in the domain of people transformation.

Connect with Yoshita Swarup Sharma