For founders at a turning point: why the plan and the person have to be read together, and a four-step way of looking before you build.
A founder at a turning point can hire a strategist, who will read the business, or a coach, who will read the person. The strategist may see that the plan is sound. The coach may see that the founder is scared. Each can be right, and the real issue only shows when the two are held together: “a sound plan won’t survive a founder who is quietly terrified of it, and no amount of coaching fixes a plan that was wrong to begin with.”
The quiet part is widespread. When Startup Snapshot surveyed more than 400 founders for its 2023 report The Untold Toll, 81% said they were not really open about their stress, fears and challenges.
The sentence about the plan belongs to Alessandra Cabra, and holding the two together is her work. She works with people and brands at what she calls an inflection point, as a strategist and as a coach. She’s the co-founder of Orange by Marmalade, a cultural branding studio for African and diaspora founders, and the founder of The Dots Connect, a coaching and strategy practice for people at the threshold of a change. What five years at board level in a London agency gave her, she says, “is the ability to read both at once, and to see where the two contradict each other.”
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See, Hold, Claim, Build
Nobody who comes to Alessandra is asked to choose between strategy and coaching. “I don’t decide in advance, and I don’t hand people a menu,” she says. “The strategist and the coach aren’t two services, they’re two depths of the same work, and the person’s inflection point tells me which depth we start at.”
The first step is the same every time, for a person or a brand: “I help them see.” Most people, she says, reach a threshold “already moving, or desperate to move, and the one thing they have skipped is looking clearly at where they actually are, tensions included.”
That is the first step of a method she uses across both practices and calls SEE, HOLD, CLAIM, BUILD. “You see what is actually there. You hold it, tensions and all, long enough to understand it rather than rush past it. You claim it, own it as yours to work with. And only then you build from it.” It runs the same way, she says, for a founder weighing whether to leave a board and for a company deciding what its brand should stand for, “because in neither case can you build anything durable on a picture you have refused to look at.”
From there, the person shows her which of the two they need. “If the block is clarity, they can’t name the shape of the decision or the brand or the next chapter, the strategist leads. If the block is meaning, they can see the situation perfectly well but can’t metabolise it, there is grief or fear or an old story running underneath, the coach leads.” Most people, she adds, “need both across the arc of the work, rarely in the same order twice.”
“The skill isn’t switching between two roles. It’s noticing when someone needs a strategy and when they just need to be heard first, because a strategy handed over too early never lands.”
Alessandra Cabra, Co-founder, Orange by Marmalade, and Founder, The Dots Connect
At Orange by Marmalade, the same four steps are applied to a company.
A Healthcare Provider in East Africa
Most companies split culture and brand, Alessandra says, “because they think culture is what happens inside the office and brand is what happens outside it. So culture becomes an HR concern and brand becomes a marketing concern, and neither is treated as the strategic infrastructure it actually is.”
Orange starts somewhere else. “There isn’t one culture in play, there are two,” she says: the culture inside the company, and the societal culture its customers live in. Cultural branding is the work of aligning them. “When those two are aligned, the brand is truthful and durable. When they’re not, the brand fractures under pressure.”
The client she gives as one of the clearest examples is a primary healthcare provider operating in East Africa. Inside its clinics, she says, everyone worked from a belief that started with the founder: “that dignity is a clinical practice, and that people who cannot pay premium prices are not people who deserve compromised care.” The families it served, as she describes them, were low-to-middle class, “building their lives, raising children,” and wanted quality healthcare they could afford “without being treated as recipients of charity.”
The brand was saying something else. Its language was affordability first (low-cost, accessible, for everyone), which placed the provider alongside those “whose customers arrive because price is the only consideration.” “Low-to-middle class families building their lives don’t want to be defined by what they can’t afford,” she says.
“We didn’t invent anything. We named what the internal company culture was already believing, we named what the actual societal culture of their customers actually wanted, and we let the external brand finally speak to that intersection.”
Alessandra, Co-founder, Orange by Marmalade
The positioning moved from low-cost to accessible excellence. The outward promise became getting patients back on their feet fast so they could keep building their lives. Inside, Orange codified what the team was already doing into a named operating framework.
When the region’s economic conditions tightened in 2024, she says, most healthcare businesses in that segment struggled to hold their positioning, and this client held. “Customers understood who this business was for. They kept coming.”
She sees the same pattern in people.
A Nursing Degree and a First Business
Asked for evidence, Alessandra doesn’t offer a single result. “The honest answer is that the evidence isn’t one result,” she says. “It’s the same pattern showing up across brands, people, and my own career.”
She gives two recent examples among the people she works with. One is a woman in her forties who was working as a PA and was, in Alessandra’s words, “certain she didn’t have what it took to go back to school and build a life around work she loved, and frightened of it besides.” She’s now in the second year of a nursing degree and closed her first year with top marks.
The other is a man in his late thirties with a corporate operations career, who is laying the ground to turn a passion for nature and adventure into his first business. “We worked through the fear and the limiting beliefs with coaching first, and I’m now his strategic consultant, setting the roadmap and the brand foundations.”
She was doing this work, she says, long before she named it.
Two Decades in Agencies
Alessandra spent two decades in creative agencies in Milan and London, independent ones and ones inside groups such as WPP and Publicis. At Rufus Leonard (now Capgemini) she was Managing Partner and then Board Director of Client Experience, with accounts that included London Business School, WWF and Royal Mail.
“At Rufus Leonard I helped people with real ability who were stuck in the wrong roles find the nerve to redirect,” she says, “and I worked with C-suite marketers to see the untold, read between the lines, and rewrite briefs that were wrong only because the picture was half complete and they couldn’t see the missing piece.”
The agency years also gave her what she calls fluency in how businesses actually work. It’s why she treats a founder’s brand problem as tangled up with how the business is run and how the people in it behave. “Carrying a board taught me to see the whole knot, and to know which thread to pull first.”
She adds a qualifier: “I am not a psychologist and I would never claim to be.” And the seat alone, she says, wouldn’t have taught her any of it. What made the difference, as she tells it, was “a temperament that couldn’t leave a half-picture alone.” “The experience gave me the material. The disposition is what turned it into a way of working.”
In 2016, when she was considering leaving marketing altogether, she started working with a coach, Amanda Davie. “She showed me the path by showing me who I am at my core, my values, my strengths, what I had actually achieved, and that let me choose from a place of knowing rather than fear,” Alessandra says. “It is no accident that helping people see themselves clearly became the centre of my own work.”
What She Learned in 2020
“In 2020, Covid took over half of our revenue almost overnight, with people’s livelihoods and their families riding on how we responded,” she says. The board pulled together, cut its own salaries, worked relentlessly and, in her words, “learned to ask for help.” She has written that during lockdown she was dressing up every morning to stay in her flat, “heels included,” and that the dress code was one of her only anchors.
The harder lesson, she says, came later.
“At the time, working myself into the ground felt like commitment. I’ve since understood it was ego, not strategy. I’d keep the same determination now and stop mistaking exhaustion for leadership.”
Alessandra, Founder, The Dots Connect
She left in 2022. She took a sabbatical, spent a few months travelling in Italy and with family and friends, and joined the Inner MBA, a nine-month course. As she puts it on her profile, “taking a step back is what we need to connect the dots and move forward intentionally and with purpose.” She trained to become a certified coach and set up The Dots Connect, and her work at Orange by Marmalade followed.
Where Alessandra Is Now
After two decades in London, Alessandra is based in Milan. Asked what’s next, she answers in one line: “Building Orange into the studio that helps define what success looks like for African founders, and rooting The Dots Connect here in Italy.”
She has also just launched a new venture, Circolo delle Fanciulle (the Gals’ Circle), which she says “will become an ecosystem of women including female-founded businesses here in the North of Italy with the vision to expand far beyond national borders.”
The readers she most wants are “founders more than Chief Execs,” and she defines them widely: “People who are already founders or have been, stopped being and want to become one again or people who have never been founders but want to take the leap.”
Her pull towards Africa is older than Orange. “I have always loved to travel and Africa was part of that pull early on. North Africa in my twenties, then Tanzania in 2016, Morocco in 2017 and Namibia in 2019. It was in Windhoek, on that last trip, that I walked into the local Ogilvy office and seriously thought about sending my CV. I didn’t, but the pull was already there. What I now do with African founders through Orange had been quietly finding me long before I recognised it.”
She has written down her vision every year since 2022. This year, she wrote, she read it back for the first time and was “astonished by how much alignment I had reached, not because I had a plan, but because I had a direction and I kept walking (and not without frequent stumbling).” She finds herself saying the same thing to clients more and more often, in the line she wants to be remembered by: “You are living your vision already. Keep walking.”
Five Lines from Alessandra’s Diary
- “Nothing real gets built until the unspoken thing is said out loud.”
- “A founder’s brand problem is almost never only a brand problem.”
- “Businesses that do this hold their shape when conditions get hard.”
- “Small things teach everything if you let them.”
- “The vision was never somewhere else. It was always here, in the daily doing and feeling.”
From the Diary of Alessandra Cabra
Alessandra Cabra is a Milan-based strategist and coach, the co-founder of Orange by Marmalade and the founder of The Dots Connect.
| Role | Co-founder, Orange by Marmalade. Founder, The Dots Connect. |
| Based in | Milan, Italy |
| Previously | Rufus Leonard: Managing Partner, then Board Director of Client Experience, 2017 to 2022 |
| Also | Harvard Business School Online: Sustainable Business Strategy, Disruptive Strategy |
“You are living your vision already. Keep walking.”
Editor’s Note
Executives Diary features Alessandra Cabra because her two practices put one question to founders that a single adviser rarely asks: what is already true here, in the business and in the person running it. The healthcare provider in East Africa is what convinces the editors, a case where, by her account, nothing was invented and the brand held when conditions tightened. Behind the method sit two decades in agencies and five years at board level, all of it before she had named the work. She looks at her own 2020 the way she asks her clients to look at theirs.
Executives Diary, Editorial
