Self-Coaching Through WorkLife Storytelling to Lead Your Way Forward

Using Your Success, Passion and Failure Stories to Keep Learning and Help Others Grow

Self-Coaching Through WorkLife Storytelling to Lead Your Way Forward. Using Your Success, Passion and Failure Stories to Keep Learning and Help Others Grow. A woman writes by a canal, beside a vineyard dinner, a talk at home and a meeting.

Self-Coaching Through WorkLife Storytelling to Lead Your Way Forward explores how we can take responsibility for the path we have chosen, keep learning from our experiences and help others find their own stories.

In Self-Coaching Through WorkLife Storytelling to Find Your Answers, Adele had begun to see her situation differently. Writing, questioning and retelling her Success, Passion and Failure Stories had helped her recognise the work that gave her the greatest satisfaction, the values she would stand by and the silence that had grown between her and her family for twenty-five years.

In Self-Coaching Through WorkLife Storytelling to Choose Your Direction, Adele returned to the family vineyard in Bordeaux. She told her stories to her brother, Luc, and listened to his, and heard her father, Henri, tell a story she had never been told. Together with Luc, Henri and Mathilde, who ran the vineyard shop, she shaped a plan everyone could stand behind. She agreed a six-month arrangement with her partner, Tom, and was honest with her chief executive, Helen, about the managing director role. By the time she flew home, she understood why she had chosen her direction.

But choosing a direction was one thing.

Leading her way forward, month after month, was another.

She had made promises to her family, to Tom and to Helen.

Now she would have to keep them, in two countries, through a harvest, a new role for Tom and a decision by the board that was still to come.

How would she take responsibility when things went wrong?

How would she help Mathilde develop, as she had once helped Priya and Gareth?

And what would her stories become as she lived the next chapter of them?

Her stories were entering a new stage.

The First Harvest

The harvest began in the second week of September.

Adele flew out for her first week in Bordeaux the same Sunday that Tom began his new role as head of department.

She left him a note on the kitchen table wishing him luck, and she felt the pull of both places before the plane had even left the ground.

At the vineyard, everything happened at once.

Luc and the pickers were in the rows from first light.

Henri, who had been told by his doctors to rest, sat at the end of the rows on a folding chair, watching everything and saying little.

The bank had agreed to restructure the loan, on condition that the vineyard showed a clear improvement in sales by February.

The family had turned down the neighbouring estate’s offer, and it would not be made again.

There was no longer a way back.

On her first morning, Adele opened her notebook and asked herself the questions she now asked at the start of anything new.

What do I need to understand before I can make a useful contribution?

What am I assuming about how things will work here?

What can I learn from the people around me?

She realised she was assuming that the commercial side could be rebuilt the way she had rebuilt the depot, with clear processes, regular reports and a plan for every week.

But the vineyard ran to the rhythm of the harvest, and during the harvest nothing else mattered to Luc.

So she spent her first two days in the rows.

She picked grapes alongside the seasonal workers, carried crates to the press and listened to Luc explain what each plot would become.

She learnt more about the wine in two days than she had in twenty-five years of visits.

On the third day, she sat down with Mathilde.

She had promised to develop Mathilde so that, by February, she could run the commercial side on her own.

Adele knew she could have written Mathilde a plan in an afternoon.

She had done that once before, at twenty-four, and her father had set it down at the kitchen table.

This time, she wanted Mathilde to write her own.

Helping Mathilde Find Her Stories

Adele gave Mathilde a notebook and asked her to write three stories from her working life: a Success Story, a Passion Story and a Failure Story.

For each one, she asked her to describe the Situation, What She Did and What It Revealed.

Mathilde looked doubtful.

She had expected a training plan, or at least a list of targets.

Adele explained that she wanted to understand what Mathilde already knew about the business, and what she cared about, before either of them decided what to do next.

Two days later, Mathilde brought the notebook back.

Her Success Story

The Situation: Three summers ago, the shop was quiet and the tastings were attracting only a handful of tourists.

What I Did: I invited the staff from four restaurants in Bordeaux to an evening tasting after their Sunday service. I talked them through each wine and told them the story of the vineyard.

What It Revealed: Two of the restaurants began ordering. People buy the wine when they know the story behind it.

Her Passion Story

The Situation: Visitors often asked whether they could order the wine once they were home. Henri said we didn’t sell that way.

What I Did: I kept a notebook behind the counter. Every time someone asked, I wrote down their name and how to contact them. After six years, there were more than four hundred names.

What It Revealed: I believed people wanted to stay connected to the vineyard, even when I wasn’t allowed to do anything about it.

Her Failure Story

The Situation: Two years ago, I asked Henri whether we could set up online sales. He told me to wait. I asked again a year later, and he said the same.

What I Did: I stopped asking. The notebook stayed behind the counter.

What It Revealed: I gave up on an idea I believed in because it was easier than asking a third time.

Adele read the stories twice.

She recognised the Failure Story at once.

It could have been hers.

She resisted the urge to tell Mathilde what the stories meant.

Instead, she asked questions.

What do your three stories have in common?

Which part of your Success Story gave you the greatest satisfaction?

What would you do with the notebook now, if you had the chance?

Mathilde thought for a long time.

Then she said that her stories were all about the same thing: people wanting a connection to the place the wine came from.

The four hundred names weren’t a list of customers.

They were four hundred people who already knew the vineyard’s story.

By the end of the week, Mathilde had written her own plan: to contact every name in the notebook, offer a small first release online and invite restaurant staff to tastings through the winter.

It started small, as Henri had asked.

It was built on what Mathilde had already proved.

And it was hers.

Adele recognised something of her own journey in that moment.

She hadn’t found her answers because someone had supplied them.

She had found them by writing, questioning and retelling her stories.

Now she was giving someone else the chance to do the same.

When Things Went Wrong

By November, the plan was beginning to work.

Mathilde’s first online release had sold out in nine days.

Three restaurants in Bordeaux had placed regular orders after her winter tastings.

Then, on a Wednesday evening in Birmingham, Adele took a call from a contact in London.

A restaurant group with six restaurants was looking for a red wine for its Christmas menus.

They wanted three hundred cases by the first week of December.

It would be the largest order the vineyard had received in years, and exactly the kind of evidence the bank wanted to see.

Adele said yes on the spot.

She spent that Saturday drafting the agreement, telling herself it was an exception.

On Monday, she called Luc with the news.

There was a long silence.

Then Luc told her there were only one hundred and eighty cases that hadn’t already been promised to Mathilde’s online customers and to the stockists she had won back.

The rest of the vintage wasn’t ready to bottle.

“We agreed Mathilde would have a say in how we sell it,” he said. “You didn’t even ask her.”

Mathilde found out the same afternoon.

She had been building a relationship with a London wine merchant for two months, and Adele had made the largest decision of the season, in the same city, without her.

When they spoke that evening, Mathilde said very little.

She didn’t need to.

And Adele realised she had given up a Saturday she had promised Tom, for a decision she should never have made alone.

Her first instinct was to put it right, fast.

She could persuade Luc to divert the cases promised to the online customers.

She could ask the restaurant group to take a different wine.

She could work through the next weekend and find a solution on her own.

She picked up her phone to call Luc back.

Then she put it down again and opened her notebook.

A New Failure Story

Adele wrote the story quickly, the way she had once written her first Failure Story.

The Situation: I found the vineyard its largest order in years, exactly when we needed it.

What I Did: I agreed to it immediately, because the opportunity might not have waited.

What It Revealed: Sometimes you have to act quickly, and Luc overreacted.

She read it back.

She recognised the shape at once: every detail pointing in the same direction, and an ending already decided.

She had seen that shape before.

So she asked herself the questions she now knew by heart.

What happened, step by step, before I decide what it means?

What did I promise, and to whom?

Who else is in this story, and how would they tell it?

Where have I seen this pattern before?

The last question stopped her.

On her first evening back in Bordeaux, under pressure, she had produced a plan in half an hour without asking Luc what he had tried.

For more than a year, under pressure, her father had carried the vineyard’s problems alone without telling anyone.

And now, under pressure, she had made the largest decision of the season on her own and given up a weekend she had promised Tom.

She had become the person in her family who carried things alone.

She wrote the story again.

The Situation: A restaurant group offered the vineyard its largest order in years, and I wanted to prove the plan was working.

What I Did: I agreed to it without checking with Luc or Mathilde. I promised stock we didn’t have, broke the one condition Luc had asked for, took a decision that belonged to Mathilde and gave up a weekend I had promised Tom.

What It Revealed: Under pressure, I decide alone, as my father did. I broke the value at the heart of my Passion Story: I made a promise I couldn’t keep. Next time an opportunity feels urgent, I need to bring the people it affects into the room before I say yes.

It was harder to read than the first version.

But it gave her something the first version couldn’t.

It told her what to do next.

She called Luc and Mathilde together.

She didn’t explain or defend.

She told them she had broken the agreement they had made, that it was her responsibility and that she was sorry.

Then she asked them what they thought they should do.

Mathilde spoke first.

She suggested offering the restaurant group the one hundred and eighty cases now, a further order from the spring bottling for their Easter menus and a tasting in London for their staff in January.

Luc agreed, on condition that Mathilde handled the call.

The restaurant group accepted.

That evening, Adele told Tom what had happened, and that the next weekend was theirs, whatever arrived in her inbox.

She had taken responsibility for her mistake.

And she had let the people around her lead the way out of it.

Keeping Her Promise to Tom

Tom had come out to Bordeaux at half-term in October, as he had asked.

He had spent a week at the vineyard, helping Luc in the cellar, sitting with Henri in the evenings and watching Adele and Mathilde work through the winter tasting list at the kitchen table.

On his last night, he had told Adele that he finally understood what she was building.

But the weeks after the restaurant order were harder.

Tom’s first term as head of department had been more demanding than either of them had expected.

There had been a difficult inspection, two members of his team on long-term leave and evenings when he came home with nothing left to give.

They kept their Sunday conversations, even when they were short.

At Christmas, as they had agreed, they sat down to review the whole arrangement.

Adele had prepared for it the way she now prepared for every conversation that mattered.

What do I want Tom to understand?

What do I need to find out?

What am I assuming?

She realised she was assuming that, because the vineyard plan was working, Tom would feel it had been worth it.

So she didn’t start with the vineyard.

She asked Tom how the last four months had been for him.

He told her honestly.

The weekend she had given to the restaurant order had hurt more than he had said at the time.

And he was proud of her, and he wanted her to finish what she had started.

Adele listened without defending herself.

Then she asked him a question she had never asked him before.

“What’s your Success Story from this term?”

Tom laughed, then thought about it seriously.

He told her about a new teacher in his department who had nearly resigned in October, and the hours he had spent helping her find her confidence again.

By December, she was running the department’s after-school club.

As he told it, Adele recognised something.

While she had been developing Mathilde, Tom had been doing the same thing in his own working life, and she had barely asked about it.

They agreed on the final two months.

Adele would keep her weeks in Bordeaux.

When she was home, her evenings and weekends would be theirs.

And from now on, their Sunday conversations would include his stories as well as hers.

Handing Over

In February, the bank reviewed the vineyard’s accounts.

The online releases had sold out three times.

Five restaurants in Bordeaux were ordering regularly, the London restaurant group had confirmed its spring order and Mathilde had signed the wine merchant she had been building a relationship with since the autumn.

The vineyard wasn’t out of danger.

But the bank agreed to extend the loan, and for the first time in two years, the figures were moving in the right direction.

Henri had found a new role of his own.

On Saturday mornings, he sat with visitors in the shop and told them the story of the vineyard, from his grandfather’s first vines to the cellar Luc had built.

Mathilde said the Saturday tastings now sold more wine than any other day of the week.

At the end of February, as they had planned, Adele handed the commercial side to Mathilde.

There was no ceremony.

Mathilde simply took over the meetings Adele had been running, and Adele stopped attending them.

On her last evening, Luc opened a bottle from the first harvest Adele had picked, and the four of them sat at the kitchen table where, twenty-five years earlier, her father had set down her plan.

On the flight home, Adele opened her notebook and wrote a new Success Story.

The Situation: The family vineyard was weeks away from being sold. My father was ill and had been hiding the problems, my brother was carrying the business alone and Mathilde’s ideas had gone unheard for years.

What I Did: After a false start, I listened first. I told my stories honestly and asked my family to tell theirs. We built a plan together. I helped Mathilde find her own stories and write her own plan, took responsibility when I got things wrong and stepped back when she was ready.

What It Revealed: I do my best work when I build something with other people and develop them so that it lasts without me. But what lasts this time includes something I didn’t plan: a family that talks to one another. The most valuable thing I helped build was the conversation.

She read it alongside the Success Story she had written about the depot merger.

The pattern was the same.

But the second story went further than the first.

It showed her that the things she built could include relationships, and that helping people tell their stories was part of how she built them.

In Front of the Board

Helen had kept her word.

She had made the case to the board, and they had agreed to hold the interviews for managing director in March.

While Adele had been in Bordeaux one week in every four, Priya and Gareth had taken on more of the operation.

Deliveries had stayed on time, and two of the depot’s best months had come while Adele was away.

She knew that was part of her case.

She also knew the board would have questions.

The evening before the interview, she sat at her kitchen table and asked herself:

What do I want the board to understand?

What am I assuming about what they want to hear?

Which of my stories will help them see how I work?

She realised she had been assuming that she needed to show the board she had never been distracted from her role.

But that wasn’t true, and she wasn’t prepared to pretend it was.

Halfway through the interview, one of the non-executive directors put the question to her directly.

“Six months ago, you told Helen you couldn’t give this role your full commitment. Why should we believe you can now?”

Adele answered with her Passion Story.

The Situation: Last summer, my father fell ill, the family vineyard was weeks from being sold and I was being considered for this role.

What I Did: I told Helen the truth, knowing it might cost me the role I had worked towards for twelve years. I committed only to what I could keep.

What It Revealed: I would rather lose an opportunity than win it on a promise I can’t keep. That’s how I intend to lead this company.

Then she told them about Priya and Gareth, and about Mathilde.

She explained that in both places, she had developed people so that the work could continue without her, and that this was how she intended to lead as managing director.

The room was quiet for a moment.

Then the director nodded and moved on to the next question.

A week later, Helen called.

The board was offering Adele the role of managing director, starting in June.

Adele thanked her, and asked for one day before she gave her answer.

That evening, she and Tom talked it through at the kitchen table: what the role would ask of them, what they would protect and what they had learnt from the last six months.

The next morning, she called Helen and accepted.

Later, she wrote the story in her notebook, beneath the Passion Story she had written about the haulage contract.

The first story had been about standing by her judgement when it was uncomfortable.

The second was about standing by the truth when it might cost her what she wanted.

The value was the same.

The stakes were higher, and this time it had been her own future on the line.

Three Stories, Retold

On a Sunday morning in spring, Adele sat at her kitchen table with the notebook she had begun the week after Luc’s call.

It was almost full.

She turned back through the pages and read her stories in the order she had written them.

Her Success Story had begun with a depot merger, when she had built something with Priya and Gareth that lasted without her.

It had grown into the story of the vineyard, where what lasted included a family that had learnt to talk to one another.

Her Passion Story had begun with a haulage contract, when she had stood by her judgement in an uncomfortable meeting.

It had grown into the story of telling Helen the truth, when standing by her values might have cost her the role she wanted.

Her Failure Story had changed the most.

It had begun as a verdict: I chose myself over my family.

Retold, it had become an honest account of the silence between them.

Told again with Luc’s and her father’s stories in it, it had shown her a family pattern.

And in November, a new Failure Story had shown her that she carried the same pattern into her own decisions under pressure, and told her what to do differently.

Adele realised her stories had never been finished.

Each time she lived through something new, the stories gained another chapter.

Each time she retold them, they showed her more of who she was and how she wanted to work.

And they had travelled beyond her notebook.

Mathilde now kept a notebook of her own, and on Saturday mornings, Henri told visitors the story of the vineyard.

On Sundays, Tom told Adele his stories from the week, and she told him hers.

The stories had become part of how the people around her understood one another.

From Self-Directing to Self-Leadership

As she closed the notebook, Adele thought about the question Tom had asked her on the night of Luc’s first call.

What did she want to do?

She could answer it now, and her answer had been tested by experience.

Self-coaching had helped her ask herself the questions that brought clarity and find her own answers.

Self-directing had helped her shape a way forward with the people her decisions affected.

The past six months had asked something more of her.

She had kept her commitments when keeping them was inconvenient.

She had noticed when she slipped into old patterns, and she had changed course.

When she got something wrong, she had said so, taken responsibility and let others lead the way out of it.

She had developed Mathilde by helping her find her own stories, rather than handing her a plan.

And she had stood by the truth in front of the board, knowing it might cost her what she wanted.

This was self-leadership in practice.

She was taking responsibility for her choices, her development and the way she worked with the people around her.

She knew the next chapter would bring new challenges.

In June, she would become managing director.

She would need to build new relationships, lead people she had once worked alongside and find out what kind of leader she would be when the decisions were hers to make.

The vineyard would have good seasons and bad ones, and her father’s health would continue to change.

She couldn’t know how every part of it would unfold.

But she had a way of approaching whatever came next.

She would keep asking herself the questions that mattered.

She would keep writing her stories, questioning them and telling them again.

And she would keep listening to the stories of the people around her.

Using Your Stories to Lead Your Way Forward

Adele’s story shows how your Success, Passion and Failure Stories can continue to guide you long after you have made a decision.

Your stories grow as you live them.

Each new experience can add a chapter to your Success Stories, deepen what your Passion Stories reveal about your values and give your Failure Stories something new to teach you.

When something goes wrong, writing it as a story can help you look beyond your first, defensive version and see what happened.

Insightful self-questions help you notice the patterns you repeat under pressure.

Effective self-feedback helps you take responsibility without excusing yourself or judging yourself too harshly, and turns a mistake into a lesson for next time.

Your stories can also help you lead others.

When you invite someone to write their own Success, Passion and Failure Stories, you help them recognise what they already know, what they care about and what they want to do differently.

They find their own answers, and they own what they build.

And when you tell your stories honestly, and listen to the stories of the people around you, you build understanding that can last.

You don’t need to know every chapter before you begin.

You can keep writing your stories, questioning them and telling them again, as your working life continues to unfold.

Self-coaching helps you find your answers.

Self-directing helps you choose your direction.

Self-leadership helps you take responsibility for the way forward.

Together, through the art of WorkLife storytelling, they offer a way to keep learning, help others grow and lead a working life that reflects what matters most to you.

Continue the Work

If Adele’s story has prompted you to reflect on your own working life, these resources offer different ways to explore your stories, ask yourself the questions that matter and find your own answers.

Explore The Art of WorkLife Storytelling — Discover how the stories we tell about our experiences can help us understand ourselves, recognise what matters and use what we learn to shape our working lives.

Explore The Art of WorkLife Storytelling Story Lessons — Practical, story-based resources that help you write your own WorkLife stories, question them and use what they reveal.

Explore The Art of WorkLife Storytelling Programmes — Follow a guided learning journey to write, question and retell your WorkLife stories, and use what they reveal to understand yourself and shape your working life.

Explore Professional Self-Coaching Resources — Work through focused resources that help you ask yourself the right questions, find your own answers and take action on what you learn.

Explore Individual WorkLife Coaching — When you need space to think with someone else about your working life, a difficult situation, a decision or what comes next, dedicated coaching sessions help you explore what matters, see your situation differently and find your own way forward.

Work With Me: Individual WorkLife Coaching, Commissioned Learning Resources, Speaking Engagements and Organisational Partnerships

Support This Work: Your support makes a difference and helps me to continue creating resources that are accessible to everyone. Thank you. Carmel

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Published by Carmel O' Reilly

I'm Carmel O'Reilly, founder of School of WorkLife. I use story-based learning — characters in real WorkLife scenarios — to help people develop their working lives, through Story Lessons, Guided Programmes, and Professional Self-Coaching resources, and the WorkLife Stories podcast. Irish, London-based, and endlessly drawn to a good story.