5M Ascent

Executive leadership mentoring for one year with I.S. Matthew, for leaders who sponsor themselves and for organisations sponsoring a senior professional.

Three sessions each month, in one of two formats: one to one through Ascent Private, or in a small group through Ascent Cohort.

I.S. Matthew reading
MentorI.S. Matthew
LengthTwelve months
RhythmThree sessions a month
FromKSh 30,000 a month

The situation

You have delivered strong results and led large teams. Yet in private, a single difficult meeting or a sudden reorganisation can leave you questioning everything you have achieved.

Leaders working at this level tend to face five career questions. Left unanswered, each one wears away at their effectiveness.

Five common career questions

The impostor narrativeAm I actually good enough for the level I am working at? One piece of harsh feedback, or a comparison with a more assertive colleague, and your record of competence seems to vanish. You keep delivering, but your confidence becomes fragile.
The mid-career plateauIs this really it for the next ten or twenty years? A deep tiredness sets in. You do not hate your work, yet you no longer feel fully alive in it.
The defence trapIf my role disappeared tomorrow, how quickly could I replace this income? Playing safe and taking fewer risks to avoid being replaced is exactly what makes a leader easier to replace.
The habit of self-censorshipWhy is my opinion set aside? Past experiences of being penalised for honesty make it harder to speak, so difficult conversations are delayed and resentment grows.
The acceleration panicIf I log off, someone else will get ahead. This is the constant fear of slowing down in a fast-moving corporate world.

What serves a leader at this point is someone further along the same path, meeting them regularly over a long enough period to see patterns of behaviour beyond single incidents, and candid enough to address them using tested frameworks.

For organisations, the senior people you are keenest to keep are often the ones with options. What keeps them is a clear sign that the organisation is investing in who they are becoming.

How the year works

Each month follows the same rhythm of three sessions.

Week oneWeek twoWeek threeWeek four
Live session with the mentorLive session with the mentorIndependent applied sprintIntegration

Two live sessions a month keep the practical work close enough to act on. The third is worked independently, against material set by the mentor. A full year gives the mentee time to make major decisions and come back with the real outcomes, so that lasting leadership habits can form.

Two formats

Ascent Private

Strictly one to one, for a senior executive who prefers to work through major career and strategic questions in complete privacy.

KSh 35,000 a month

Ascent Cohort

A carefully chosen small group, for a rising leader who gains from observing and sharing insights with trusted peers.

KSh 30,000 a month per participant
Minimum of two leaders sponsored

Both formats run for twelve months, with two live sessions and one independent session each month. Fees exclude VAT and are paid annually or quarterly in advance.

The curriculum

The material comes from both my books. In Stitch In Time, I set out the institutional frame, which helps the mentee read and diagnose their organisation and stop taking its frictions personally. In 5M Unbreakable, I set out the personal frame, and the year works through its five parts.

In 5M Unbreakable, I describe being unbreakable as having an inner structure that can bend under strain without snapping.

PhaseThe question answeredThe framework built
ProofThe impostor narrative: doubt about working well at executive level.The Value Registry. A running record of evidence of the value you create, reviewed on a set schedule.
PivotThe mid-career plateau: restlessness and the next strategic move.The Experiment Ledger. A structured view of career options, each turned into a low-risk, measurable experiment.
ProtectionThe defence trap: the fear of becoming replaceable.The Capability Audit. An honest exposure audit with a plan to build skills that are rare, hard to copy and easy to redeploy.
PowerSelf-censorship: hesitation to speak up or handle high-stakes conflict.The Truth Protocol. A clear method for raising difficult realities, prepared so the message is delivered in full.
PeaceThe acceleration panic: the fear that rest or boundaries will cost your position.The Personal Governance Charter. A personal maintenance schedule with firm boundaries, managed like a governance document.

What a year produces

The mentee ends the year having worked through several consequential professional decisions with an experienced practitioner beside them, holding them to account for the outcomes.

Organisations sponsoring a leader can expect to see:

  • Sharper judgment. Better composure and clearer thinking in hard, high-stakes conversations.
  • Ownership of solutions. A leader who brings clear options and recommendations along with the problem.
  • A steady hand. Clear accountability and composure when a project or unit faces failure.
  • Constructive dissent. A willingness to disagree professionally and protect the organisation from groupthink.

Complete confidentiality

No reports, session summaries or HR assessments are produced for the sponsoring organisation. What passes between mentor and mentee stays between them, so the mentee can speak freely and grow.

For founders, SME and non-profit leaders

Mentoring for Founders, SME and Non-Profit Leaders is a version of 5M Ascent for leaders who hold too much of their organisation in their own hands. It follows the same rhythm and gives the greatest share of time to Core Load and Everyday Work, so the strain on the leader eases early in the year.

About Mentoring for Founders

Begin with a free consultation

A forty-five-minute conversation between you and I.S. Matthew, with no charge and no obligation on either side. Together you look at the career questions that press on you hardest and choose the right format. Once both of you agree to go ahead, the start date is set.

WhatsApp @is5ML