Considering coaching but not sure what to expect?

Welcome to my Journeys in coaching blog series. Join me as I share composite stories that authentically reflect the transformative process and profound shifts in perspective that resulted from real coaching sessions. They offer valuable insights and strategies you can apply in your own life and work. Get a genuine feel for my approach, and the type of breakthroughs and paradigm shifts that can emerge when a coach and coachee explore pivotal moments together.

The delegator’s dilemma

Have you ever found yourself caught between knowing you must delegate and doubting if your team is truly ready?

Andrea, a composite character from several founders I've coached, faced this tension while steering her growing tech company towards a new market segment.

During our third session, she sat rearranging sticky notes, afternoon light casting shadows across her office. The usual spark in her eyes had dimmed, she looked tired.

"I know I need to delegate more," she began. "But we're mid-pivot, and I'm not convinced my team really gets the vision or can maintain our standards."

I nodded slightly, creating space for her to continue.

"It's like I'm trying to hand over the controls of a plane while changing course mid-flight," she said. "If I let go now and someone steers even slightly off course, we could miss our destination entirely."

Although Andrea expressed concern about this crucial juncture, I sensed something else underlying her words.

"I'm curious—have you experienced a different kind of journey, one where course corrections feel more natural?"

Andrea tilted her head. "What do you mean?"

"Well, when flying a plane, mistakes can be catastrophic. What about other ways of reaching destinations?" I asked.

"Like driving a car on a road trip," she said slowly. "I always did that with my friends. If you miss a turn, you can always find another route."

"Based on your experience, which metaphor feels more accurate?"

Andrea leaned forward, "It's not like it's always been a smooth ride, but I've always felt I had time to course correct."

How is it different this time? I challenged.

"When I started, I had nothing to lose," she said quietly. "Now that something has been built, I'm afraid to lose it. Letting go at this juncture is a real struggle."

Despite her insight, in our next session, Andrea still felt stumped.

"What happens if you continue being the only one who can steer?" I ventured.

"We crash anyway. Either from my burnout or our inability to scale."

During our eighth session, Andrea looked slightly more relaxed than before. When I asked what had shifted, she described her small delegation experiments. "It's uncomfortable. I'm still learning to sit with that discomfort."

"What's helping you stay with it?" I asked.

"Remembering the road trip," she smiled. "Remembering that we are driving, not being launched into space."

A year later, as we concluded our work, I asked what she would take with her.

"The biggest shift was in acceptance. I had to learn to breathe again—to trust the process, even when things are done in a different way. I still suck air through my teeth sometimes, but I'm no longer reaching for the wheel at every turn."

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What metaphors might be shaping your approach to delegation? How could reframing them open new possibilities?

When Authenticity Requires Difficult Choices

Have you ever wondered if your commitment to develop every team member might conflict with your responsibility to protect the whole team and mission?

Nadia, a composite character from several leaders I've coached, faced this dilemma with a talented specialist, Josh, whose brilliant innovations came packaged with behaviours that steadily eroded team trust.

During our third session, Nadia was visibly frustrated as she recalled months of interventions and dashed hopes.

"I've tried everything," she said. "Regular feedback sessions, structured expectations, training.... What's worse, it requires me to adapt my leadership approach to such an extent that it's eroding the team culture I've built!"

"When you say you've tried feedback, how direct were those conversations?" I probed.

Nadia paused. "I suppose I've been... diplomatic. Focusing on specific incidents rather than patterns. Balancing critiques with praise. Maybe too balanced."

"What would you tell a friend facing this situation?" I asked.

"That they have someone on their team who's unable to acknowledge mistakes, who deflects feedback. That they are not being honest enough about the severity of the problem."

Through our sessions, Nadia gained critical insights:

She recognised her commitment to individual growth had placed one person's development above team wellbeing. Her "diplomatic" approach prevented Josh from understanding the gravity of the situation.

She understood she had been having the conversations she could tolerate, not the ones that were needed. Nadia's discomfort with conflict had masked itself as care and development.

In one of our final sessions, Nadia appeared both sad and relieved. She had developed enough confidence to have the candid conversation with Josh she had been avoiding.

"It didn't go perfect," she admitted. "He was defensive, accused me of suddenly changing expectations. I realised my previous 'candour' had been so diluted he never truly heard it."

Six months later Nadia and I had a casual check in.

"How's the team?" I asked.

"When the situation was resolved, change emerged over the following weeks. Things had deteriorated more than I realised. Now that I can be more consistent in my leadership approach, we are starting to operate with a higher level of trust"

"Also, something unexpected happened last week that I would like to explore further. I received an email from Josh. He wrote that while he still felt blindsided, the conversation was the first time someone had been completely straightforward with him without either sugar-coating or attacking. He'd started to recognise some patterns in his new role."


What difficult truths are you avoiding?

Where are you choosing comfort over your responsibility to provide genuine feedback?

Leveraging Organisational Values Against Office Politics.

Have you ever felt the ground shift beneath your professional feet? Andrew, a composite of leaders I've coached, found himself at such a crossroads.

Tasked with leading an additional team, he was also impacted by an increase in office politics following a recent restructuring.

In our second coaching session, Andrew sat with his jaw clenched, fingers drumming against his mug—a stark contrast to the spring colours of the art-café where we met.

"I'm caught in an impossible situation," he said. "I want to shield my team, yet some members are shifting allegiances, impacting productivity. It's hurtful. I'm frustrated by the effectiveness of these underhanded tactics."

"It seems we're circling around something else here?" I asked.

"I could deploy similar tactics—I see how it works. It's not that I couldn't. I don't want to!" Andrew exclaimed.

"Can you explain to me how it works then?" I asked.

Andrew's expression shifted. "Fair call—I couldn't. I've been so focused on surviving that I haven't charted the tactics or challenged the games being played."

"How would you challenge the game itself if you had more space?" I asked.

"I don't know," Andrew answered honestly.

His acknowledgement opened a path to insights that emerged between sessions:

By his fourth session, Andrew realised how reactive he'd become. What upset him most was the disconnect between the organisation's official standards and unofficial practices.

"Where is the strategic high ground here?" I asked.

After a silence, his eyes lit up. "The organisation's stated values offer a lever I haven't pulled yet."

Using these values allowed Andrew to become more transparent in his communication about what was happening. "Underhanded tactics thrive in silence," he noted in our fifth session. As he adapted his communication strategy, his ability to manage the situation improved.

Later, Andrew looked more relaxed. "I'm no longer flailing to fend off everything—I'm picking my battles. Since I started calling out behaviours, colleagues who see the same danger to the organisation have approached me. I feel less alone."

By our final session, Andrew had experienced a significant perspective shift, enabling him to adopt a more effective stance—purposefully navigating organisational politics while pushing back on damaging behaviours with integrity.

What political dynamics are you facing, and how might they be inviting you into a more nuanced expression of your leadership?

𝗕𝗲𝘁𝘄𝗲𝗲𝗻 𝗧𝘄𝗼 𝗪𝗼𝗿𝗹𝗱𝘀, 𝗪𝗵𝗲𝗻 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗧𝗿𝗮𝗻𝘀𝗶𝘁𝗶𝗼𝗻𝘀 𝗕𝗲𝗰𝗼𝗺𝗲 𝗨𝗻𝗲𝘅𝗽𝗲𝗰𝘁𝗲𝗱 𝗧𝗲𝗮𝗰𝗵𝗲𝗿𝘀.

Have you ever noticed how the most profound insights come from our most uncomfortable transitions?

Elena, a senior leader with a 15-year career in healthcare technology, faced a crossroads when her mother's health deteriorated. Living in Spain while her parents were in Sweden created an impossible situation. After difficult conversations, she and her partner decided to relocate.

Elena negotiated a 7 month leadership transition—enough time, she believed, to complete key initiatives and transfer her team of 23 and relationships to her successor.

During our third coaching session, Elena placed her notebook on the table with unusual heaviness.

An hour in, I asked: "What is making this so tough?"

"In the strategy meeting I maintained composure. Everyone thought I was fine," she said, hands trembling slightly. "But inside? I felt like I was grieving something I hadn't expected to lose."

I remained silent, sharing the moment with her.

"What am I really grieving here?" she finally said.

As Elena explored her inquiry, I was reminded of William Bridges' insight about acknowledging necessary endings before new beginnings can emerge.

In the following two months, Elena arrived for our sessions sometimes speaking rapidly, other times sitting in contemplative silence.

"It's like I'm helping someone redecorate a house I built brick by brick while still living in it," she said, looking out the window. "And I feel a responsibility to make it look effortless."

"Are there lessons in this experience you couldn't unlock any other way?" I ventured.

As weeks passed, Elena uncovered insights that surfaced naturally:

She gained a rare perspective few leaders experience. "I understand leadership differently now. I knew how to lead from the center. What I've learned is to operate effectively from the periphery."

She developed deeper self-compassion. "When I stopped criticising myself for feeling loss, I found more energy for what mattered."

Most significant was her understanding of presence. "I used to think good leadership meant always being there," she reflected during our final session. "Now I understand the power in discerning when to let go and when to be fully present."

By our last meeting, Elena had transformed necessity into a catalyst for growth—carrying these insights into her new leadership role.

For leaders navigating similar transitions: your feelings are valid. This type of experience, while difficult, can become wisdom that serves your entire career.

What transition are you navigating, and what unexpected wisdom might be waiting there?