William (Bill) Best · Corporate advisory, C-suite and board coaching
Counsel from someone who has carried the decision.
Garrett Lane Advisors is the practice of William (Bill) Best — over four decades as a chief executive, chief operating officer, chief financial officer and board member across real estate, mining, wealth and investment management, banking, fintech and professional services, and more than 120 M&A transactions and financings completed on both sides of the table.
Growth and scale, transactions and integrations, restructurings, governance, and the succession conversations nobody wants to start. Hands-on, not theoretical.
Garrett Lane Advisors
40+Years in operating and board roles, C-suite throughout
120+M&A transactions and financings completed — buy side and sell side, debt and equity
$675M → $4.25BAssets rebuilt since 2016, with revenue from $10.9M to $32.7M
12.8×Profitability growth — with EBITDA compounding at 27.4% a year across the five years from 2021
$850M+Debt restructured as lead restructuring officer
Five practices, one practitioner
01
Corporate advisory
Standing counsel to owners, chief executives and boards on growth, scale, operating model and turnaround.
02
CEO & C-suite coaching
Confidential one-to-one work with chief executives and their direct reports, aimed at judgement rather than technique.
03
M&A, capital raising & financing advisory
Transaction readiness, debt and equity raising, buy- and sell-side support, and the integration that follows the close.
04
Board effectiveness
Board and committee reviews, director development, succession and the governance architecture underneath both.
05
Team facilitation
Top-team alignment where the strategy is agreed on paper and the executive group is not agreed in practice.
— Position
Why one adviser
A large firm sends a team, a methodology and a deck. That is the right answer for some problems. It is the wrong answer for a chair deciding whether to move on a chief executive, or a CEO deciding whether to tell the board how bad it actually is.
Those conversations need one person who carries the whole context and is accountable for the advice. I have sat in the operating seat for a turnaround, a consolidation, a court-supervised restructuring, a post-merger integration and a capital raise — not advised from the outside while someone else lived with the consequences.
Work is deliberately limited to a small number of engagements at a time, and I decline anything where I already act for a competitor or a party on the other side of a live transaction.
— Clients
Who I work with
Founders, owners and family offices deciding whether to professionalise, sell, or hand over
Chief executives and C-suite leaders in a step-up role or a first twelve months
Chairs, lead directors and nominating & governance committees
Private-equity and venture-backed boards through growth, scale and exit
Businesses in turnaround, restructuring or post-merger integration
Parties on either side of a transaction — preparing for one, running one, or living with one that has already closed
— Reach
Sectors and markets
Sectors
Real estateDevelopment, construction, investment and management — retail, residential and mixed use
Mining and resourcesExploration through financing to initial production
Wealth and investment managementAdvisory channels, platforms and asset growth
Banking and financial servicesCorporate banking, real estate lending and syndications
FintechPlatform businesses and the operators who have to run them
Professional servicesPartnerships, practice economics and post-merger integration
Markets
North AmericaUnited States and Canada, with particular depth in Canada
EuropeParticularly the United Kingdom and Ireland
AfricaSub-Saharan, from mining and resource financing
Australia and New Zealand
Based in Chicago and Toronto. Outside these sectors the practice is largely sector-agnostic — the questions a board faces do not change as much as the industry language does.
A first conversation costs nothing.
Ninety minutes on the decision actually in front of you. If it is useful, we talk about what a working arrangement looks like. If it is not, it is not.
Services
Five kinds of work, usually in combination.
Most engagements begin in one of these and grow into another. A board review surfaces a chief executive who needs a coach; a coaching engagement surfaces a top team that cannot decide.
Toronto financial district
01
Corporate advisory
Counsel to the owner, chief executive or chair on the decisions that set the next three years: where to compete, what to stop, whether to buy, how to fund it, when to hand over. I am not a substitute for your bankers or your lawyers — I am the person you think with before you instruct them, and the one who has already sat on your side of that table.
For: Owners, CEOs and chairs facing a decision with no clean precedent.
Typically covers
Strategy formation and stress-testing before it reaches the board
Growth and scale planning, including the operating model that has to carry it
Turnaround, restructuring and crisis management
Technology and systems decisions judged as business decisions
Ownership and executive succession, internal and external
02
CEO & C-suite coaching
Confidential, structured, and pointed at judgement rather than technique. The early sessions map how you actually decide, who you actually listen to, and where your reputation is running ahead of or behind your performance. The later sessions are about what you do differently on Monday. I coach chief executives through Entrepreneurs' Organization in Chicago and have done this work privately for years.
For: Sitting chief executives, successors in waiting, and C-suite leaders in a step-up role.
Typically covers
Stakeholder-informed 360 at the start, repeated at close
Decision quality, delegation, and where your time actually goes
Authority and presence with the board, investors and the market
Building a cohesive senior team, and developing the people in it
Handling a direct report who is respected, productive and corrosive
First-hundred-days work for newly appointed executives
03
M&A, capital raising and financing advisory
More than 120 completed transactions — buy side and sell side, debt and equity — advised and run from inside the business rather than beside it: US$80 million of equity and $19 million of debt raised across twenty-three mining properties; a consolidation of Canada's independent financial advisory channel; a post-merger integration across a 750-partner firm; and a court-supervised restructuring of more than $850 million of debt. Plenty of advisers have closed a deal. Fewer have run the company on the Monday after it closed, which is where the value is usually won or lost.
For: Owners, CEOs, CFOs and boards preparing for a transaction, running one, or living with one that has already closed.
Typically covers
Transaction readiness — the numbers, the systems and the story made fundable before anyone is approached
Buy-side and sell-side strategy, target screening, and a sense-check on valuation
Debt and equity raising, including first institutional rounds and private-equity processes
Diligence management and negotiation support alongside your bankers and lawyers
Post-merger integration: operations, systems, people, and the C-suite that has to run the result
Refinancing, restructuring and distressed situations, including court-supervised processes
Founder and family liquidity — partial sales, recapitalisations and ownership transitions
04
Board effectiveness & governance
Most boards do not have a governance problem on paper. They have a behaviour problem in the room: the same three people speak, dissent arrives in the car park, and the papers are so long that nobody reads to the end. A review names that plainly — to the chair first, then to the board. Certified in governance and climate & ESG competence by Competent Boards (GCB.D, CCB.D), and currently a non-executive chair and director.
For: Chairs, lead directors, company secretaries and nominating committees.
Typically covers
Board and committee effectiveness reviews, internally or externally facilitated
Director interviews, meeting observation, written findings and a working session
Board composition, skills matrices and chair succession
Onboarding and development for first-time directors
Audit and risk, compensation, and nominating & governance committee practice
ESG, climate and biodiversity governance: what a board is actually accountable for
Family office governance and the move from ownership to oversight
Board–management interface: papers, cadence, and what is decided where
05
Executive team facilitation
An executive team that agrees in the meeting and relitigates it afterwards does not have a communication problem; it has an unresolved disagreement about priorities, or about who decides. Facilitation here is not an away-day with flipcharts. It is getting the real disagreement on the table while everyone is still in the room — the same work I led through two post-merger integrations and a channel consolidation.
For: New executive teams, merged teams, and teams that have quietly stopped arguing.
Typically covers
Confidential diagnostic interviews with each member before any session
Facilitated sessions on priorities, decision rights and accountability
Post-merger and post-restructure team integration
Conflict between two senior leaders the organisation is working around
Follow-through one-to-ones so the session survives contact with the calendar
Not sure which of these it is?
That is normal, and working it out is usually the most useful first hour. Describe the situation and I will tell you plainly whether I am the right person for it.
How I work
Direct, structured, and on a clear clock.
Every engagement is scoped in writing before it starts: what we are working on, how long it runs, who else is told, and what would make it a success. Nothing rolls on indefinitely without a review.
— Principles
Four commitments
Candour is the deliverable
You can buy agreement anywhere. If I think a decision is wrong, you will hear it in the session rather than in a carefully worded summary afterwards. Clients describe the style as direct and fair, in that order.
Confidentiality has a defined edge
What you say stays with me. Before we begin we agree exactly what is reported to a sponsor or a chair — usually themes and progress, never content — and you see anything written about you before anyone else does.
Advice comes with a plan attached
Problems are easy to name. The work is the system, the sequence and the people that fix them, with quality processes put in place so the improvement survives my leaving.
Engagements end
The aim is that you need me less, not more. Every engagement has a defined close and an honest conversation about whether continuing adds anything.
— Formats
Shapes an engagement takes
Format
Shape
Typical span
First conversation
One session on the decision in front of you. No obligation either way.
90 minutes
Coaching engagement
Fortnightly sessions, stakeholder input at the start, formal review at six months. Taken as an annual commitment — the work that changes how someone leads does not fit in a quarter.
12 months
Advisory retainer
Standing counsel to an owner, CEO or chair: monthly cadence plus access between meetings.
6–12 months
Board review
Interviews with every director, observation of two meetings, written findings, working session.
8–12 weeks
Team intervention
Diagnostic interviews, two facilitated sessions, follow-through one-to-ones.
10–14 weeks
Board seat
Non-executive director, advisory board member or committee chair — audit and risk, compensation, nominating and governance — where the fit is right and the conflicts are clear.
By appointment
Fees
Engagements run on a monthly retainer, scoped and agreed in writing before any work begins — no hourly billing and no meter running between sessions.
Where an engagement has a defined, measurable outcome — a transaction closed, a financing raised, a target delivered — part of the fee can be structured as a success fee, agreed at the outset so that a share of the cost sits with the result rather than the calendar. Coaching and board effectiveness work is retainer-only: independence there is worth more than the upside.
Work is delivered as a mix of in-person and remote sessions — board reviews, team facilitation and first meetings in the room; regular coaching and retainer sessions remote unless there is a reason not to be. Travel outside Chicago and Toronto is billed at cost.
— Start
What a first conversation looks like
Before. You send two or three paragraphs on the situation. Nothing formal, no documents needed.
During. Ninety minutes, mostly you talking and me asking. By the end you should have at least one thing you had not considered.
After. A short note from me: what I heard, what I would do, and whether I am the right person for it. Sometimes the answer is that you need a lawyer, a banker, or nobody at all.
Then. If we go ahead, a one-page engagement letter — scope, duration, confidentiality, fee — before any further work.
Support services
The practical work behind a move.
Advisory and coaching deal with the decision. These services deal with what the decision requires of you in public: a résumé that survives a search committee, a board bio that reads like a director’s, a profile that matches the career behind it, the ability to hold a room in an interview, and a way of describing forty years in thirty seconds.
They are delivered by Alice Bradley, a specialist I work with, rather than by me — because this is a craft, and it is not mine.
01
Résumé and bio writing
Most senior résumés are a list of roles held rather than a case for the next one. The work here is to find what you were actually accountable for, put a number against it, and order it so a search consultant reaches the relevant part in the first fifteen seconds. Separate pieces for separate purposes: an executive résumé, a board bio, a short-form biography for conference programmes and announcements.
For: Executives in or approaching transition, and directors building a board-ready profile.
Typically covers
Executive résumé — built around accountability and measurable results, not duties
Board bio, written to what a nominating committee actually screens for
Short-form biography for programmes, announcements and introductions
Cover letters and approach notes for specific roles
Applicant-tracking formatting, so the document survives the software before it reaches a human
02
LinkedIn optimisation
For most senior people the profile is dormant, years out of date, and the first thing anyone checks before a call. Search consultants and committee members look there before they look anywhere else. The work is to make the profile say the same thing as the résumé, in the register of the platform, and to make it findable by the people who are looking for someone like you.
For: Anyone whose online profile is running several years behind their career.
Typically covers
Headline and About section rewritten to position rather than describe
Experience entries aligned with the résumé, with the results kept in
Keyword and skills work so recruiter searches actually surface you
Recommendations and endorsements — who to ask and what to ask for
A light, sustainable posting approach for those who want visibility without a second job
03
Interview coaching
Senior interviews are not competency tests; they are a judgement of how you think under mild pressure with people who have already read your résumé. The preparation is rehearsal with honest feedback: your story in ninety seconds, the difficult chapter told without defensiveness, and the questions you ask — which is where most candidates are actually assessed.
For: Executive candidates, first-time directors, and anyone facing a panel or a nominating committee.
Typically covers
Your narrative — why this role, why now, why you — in ninety seconds
Rehearsal for the hard questions: a gap, an exit, a failure, a number that went the wrong way
Board and nominating committee interviews, which follow different rules
The questions you ask, and what they reveal
Recorded practice with structured feedback, and a second pass after you have worked on it
04
Personal branding and the elevator pitch
At this level, your reputation precedes you into rooms you are not in. The work here is to decide what you want it to say, make it consistent everywhere someone might check, and give you a version of it short enough to say out loud. Most senior people have a forty-year career and no way of describing it in thirty seconds without sounding either modest or insufferable.
For: Anyone stepping into a market — a search, a board seat, a new practice, a speaking circuit.
Typically covers
The positioning question first: what you want to be called for, and by whom
The thirty-second version, the two-minute version, and the one line under your name
Consistency across résumé, board bio, LinkedIn, conference programmes and introductions
How to introduce yourself in a room without listing your job history
What to say about a career change, a gap, or a step down — before someone else frames it
A visible presence you can actually sustain, rather than one that lapses in a month
— How it works
Engaging these services
Introduced through me. Tell me what you need and I will make the introduction, with context, so you are not starting from a blank page.
Engaged directly. The engagement, the scope and the fee are between you and Alice. I take no referral fee, no commission and no share of it.
Independent of any advisory work. You can use these services without engaging me for anything else, and engaging me does not oblige you to use them.
Confidential. A job search is usually a private matter. Nothing about an introduction goes anywhere else.
The specialist
Alice Bradley has spent twenty-five years in executive search, leadership development and community building, supporting C-level leaders through moments of profound change.
She works with senior executives on personal brand, career shifts and the strategic networks that open the hidden job market — much of which never reaches an advertised role. She is a chapter manager at YPO, connecting chief executives and presidents across industries, and the founder of Eagle, which helps experienced leaders turn hard-won experience into ventures that address real problems.
A first-class honours degree in business and management, earned as a mature student while working, and three marathons — which she credits for what she knows about endurance, mindset and the value of showing up.
“Helping others see the best in themselves — and do something extraordinary with it.”
Tell me what you are preparing for — a search, a board seat, a panel next month — and I will point you to the right piece of this.
Track record
Results I was accountable for, not ones I observed.
Advisory and coaching engagements are confidential and are not described here; named references are available privately, with the client's consent, to organisations in live discussion. What follows is from the operating seat.
Chicago · 333 West Wacker
Wealth & investment management
A US wealth & investment management firmPartner, COO & CFO · 2014–present
Situation
A $675M asset business with ailing operations and management information too thin to run it on.
Work
Restructured for growth around people and process, built a more capable and structured team, and championed a $1M investment to digitise the business end to end — asset management through to fee generation.
Result
Assets grew to $4.25B and revenue from $10.9M to $32.7M, with profitability up 12.8× and EBITDA compounding at 27.4% a year across the five years from 2021.
Commercial real estate
A private equity & commercial real estate businessManaging Principal · 2012–present
Situation
A shopping mall bought for its $16M debt, losing $300K a year and serving a demographic it had never been designed for.
Work
Repositioned the centre for the Hispanic and Disney tourist communities on a $7M investment, including a new 'Marketplace' format that converted casual traders into permanent tenants.
Result
Foot traffic from 400K to 1.7M a year, occupancy from 40% to 100%, and losses reversed to over $7.0M revenue and $3.8M NOI.
Wealth management
A Canadian wealth management groupPresident & CEO, COO, Board Member · 1995–2000
Situation
A wealth management business inside an industry consolidating the independent financial advisory channel in Canada.
Work
Full P&L accountability for the operating company, and chief operating officer of the advisory arm through the consolidation, with a seat on the parent board.
Result
Net operating profit up 11.5× over four years on 40% top-line growth, and the firm twice named one of Canada's 50 Best Managed Private Companies.
Professional services
An international law firmChief Operating Officer · 2003–2006
Situation
A 750-partner international law firm carrying an unintegrated merger and no C-suite.
Work
Built the firm's first C-suite team, delivered the post-merger operational integration, established domestic and international offices, and put in a practice- and industry-focused marketing and branding structure.
Result
Revenue up 36% and profit up 40% under full P&L accountability.
Restructuring
A real estate development groupEVP & Chief Operating Officer · 1989–1995
Situation
A real estate development group carrying over $850M of debt into a court-supervised restructuring.
Work
Lead Restructuring Officer through the CCAA process, alongside 23 property dispositions, 14 acquisitions, 12 retail developments, 10 expansions and 10 residential and mixed-use projects.
Result
Occupancy lifted from 93% to 97.7% with average rental rates held through the restructuring.
Mining & resources
An exploration & mining groupChief Financial Officer · 2008–2012
Situation
An exploration and mining portfolio in the Democratic Republic of Congo needing capital and a route into production.
Work
Raised US$80M in equity and $19M in debt across 23 exploration and mining properties.
Result
One site taken through to initial production.
— In their words
What clients say
“
I have had the pleasure of working with Bill Best for almost a decade. If you have the opportunity to have Bill in your corner as an advisor or board member: take it! His strategic insight, extensive experience, deep trustworthiness and genuine care are transformational.
Grant Henzel · Founder & CEO Entrepreneurial Capital and NPM LLC
“
Working with Bill has been incredibly valuable to me as a business owner and CEO. He brings a depth of business experience and a true understanding of how all parts of an organization work together — from strategy and operations to leadership, finance, and growth.
Bill has helped me clarify where I want to take the business, build the framework to get there, and stay focused on execution. His perspective is consistently sharp and practical, and I rely on him when I’m working through complicated decisions or challenges. He has a remarkable ability to quickly see what matters most and help me find a clear path forward.
What I appreciate just as much is how he works. Bill is no-nonsense, approachable, and direct, while bringing a tremendous amount of heart to the relationship. He understands both the business and the person leading it. I’m a stronger leader — and my company is stronger — because of his input.
Anna Loibner Davidson · Founder & CEO Blackberry Market
References on request.
If we get to a serious conversation, I will introduce you to people who have worked with me — with their permission, and in their own words.
About
William S. Best
CPA, CA, GCB.D, CCB.D — Founder & CEO, Garrett Lane Advisors. Over four decades in the C-suite and the boardroom, across eight industries and three continents.
Toronto, from the lake
Over four decades in senior operating and board roles across banking and financial services, wealth and investment management, real estate, professional services, consulting, fintech, retail and mining — in organisations ranging from small family offices to large listed corporations. The common thread is hands-on accountability: M&A, debt and equity financings, operations, finance and accounting, cash and asset management, technology and systems integration, human resources, and strategy that had to be executed rather than presented.
The fascination with business started at Coopers & Lybrand, auditing banking and retail clients and seeing how differently well-run and badly-run companies behave from the inside. A qualified chartered accountant by training, the career since has been operational: chief executive of one of Canada's premier wealth management firms; chief operating officer and board member of one of Canada's largest independent financial advisory firms through its consolidation of the independent channel; chief operating officer of one of Canada's largest international business law firms; and partner, chief operating and chief financial officer of a US wealth and investment management business taken from $675M to $4.25B in assets.
Advisory work grew out of the board seats. Directors kept asking the same questions in the room and different ones in the corridor, and chief executives kept needing somewhere to think out loud that was not their board, their investors or their team. Garrett Lane Advisors exists to be that place — with the bias toward problems identified plainly, strategies built around people and process, and quality systems put in place so the fix outlasts the engagement.
Outside the work: family, travel, and endurance sport. Seven full Ironman races, eleven half Ironmans, six marathons, a finish at the 2013 Ironman World Championship, and an Ironman coaching certification — which turns out to be reasonable preparation for advising people on things that take years and hurt in the middle.
A separate practice
Ironman coaching and inspirational speaking run under their own name, with their own site. [Second site launching — name and URL to follow.]
Below: current thinking on corporate strategy and governance that is worth a chief executive's time, with a note on why. Then my own occasional writing, published when there is something worth saying rather than on a schedule.
Pedro Fontes Falcão and Randall S. Peterson argue that the chair's job has outgrown the executive résumé that usually wins it. The skills that matter now are synthesis, facilitation, psychological safety in the room, and balancing interests that genuinely conflict.
Why it mattersAlmost every board review I have seen confirms this. The chair's technical credibility is rarely the constraint; the ability to get six directors to disagree productively in ninety minutes is.
Seven priorities, of which four are new in substance: scenario planning as a standing board activity, governance frameworks for autonomous AI agents, resilience over prevention in cyber, and a hard look at whether committee remits still cover the risks without overlapping.
Why it mattersUse it as an audit, not a reading list. Take each item to your own board calendar and ask where in the year it is actually discussed. Most boards find three with no home.
Technology infusion, economic and geopolitical disruption, and a workforce whose expectations and demographics have both shifted — with the conclusion that sustained performance, not short-term gain, is what the structural response has to be built for.
Why it mattersThe forces are not controversial. The useful question is which of your operating processes were designed before all three were true, and what it would cost to redesign them.
Deal value at its second-highest year on record, driven by three motives: buying a position in AI, adapting to fragmented post-globalisation markets, and chasing profit pools that are moving faster than organic strategy can follow.
Why it mattersDeal logic has rarely been the failure point in the transactions I have worked on. Integration capacity has. Read the value-creation chapter before the volume charts.
Harvard Law School Forum on Corporate Governance · February 2026
On the gap between boards that receive AI updates and boards that govern AI — oversight of deployment, data, workforce consequences and accountability when a system rather than a person makes the call.
Why it mattersThe certification I hold in governance and climate competence exists because governance frameworks lag the risk by about five years. AI is the current instance of that lag.
— Writing
Articles
September 2026 Governance 6 min
September 2026 Turnaround 8 min
September 2026 Succession 7 min
Insights · Governance · September 2026 · 6 min read
The dissent that arrives in the car park
Boards rarely fail because directors disagree. They fail because the disagreement surfaces after the vote, in ones and twos, where it cannot change anything.
The meeting runs to time. The paper is taken as read. The chair asks whether there are any questions, there is a pause of about four seconds, and the resolution is carried. Forty minutes later, in the car park, a director tells you what they actually thought of it.
I have sat on boards and run board effectiveness reviews for long enough to know that this is not an occasional failure. It is the normal condition of a great many perfectly respectable boards, including some with immaculate governance frameworks, fully independent committees and an annual evaluation that comes back clean.
The problem is not that directors disagree. Disagreement is the entire reason a board exists — if the board always reached the same conclusion as management, you could save everyone a lot of money by abolishing it. The problem is where the disagreement surfaces. Inside the room it is governance. In the car park it is gossip, and it is worse than useless, because it gives the dissenter the comfort of having been right without the inconvenience of having said so.
Why it happens
Four causes, in my experience, and none of them is that the directors are weak.
The papers. Two hundred pages circulated on the Friday for a Tuesday meeting. Nobody reads to the end. A director who has not read page 140 will not risk a question that page 140 may already have answered, so they say nothing.
The order of speaking. The longest-tenured director speaks first, frames the issue, and everyone who follows is now agreeing or disagreeing with a colleague rather than assessing a proposal.
The presence of management. It is difficult to say “I am not convinced by this plan” to the face of the executive who wrote it, worked on it for a quarter, and will have to deliver it. Most people are polite before they are rigorous.
The cost of being the one. Objecting once is fine. Objecting twice makes you the difficult director. Objecting three times and you are not on the shortlist for the next board.
What it costs
The obvious cost is the bad decision that nobody stopped. That is the rare one. The ordinary costs are quieter and more corrosive.
Decisions get relitigated. A resolution passed without real assent comes back in three months wearing a different hat, and the executive team learns that board approval is provisional. Management stops being able to read the board, because the signal in the room and the signal in the corridor point in opposite directions. And the board’s collective judgement — the entire asset you have assembled and pay for — is never actually applied to the decision it was assembled for.
What a chair can actually do
This is a chair’s problem to solve. Not the company secretary’s, not the evaluation consultant’s. Six things, in the order I would do them.
Fix the papers. A ten-page limit, and a one-page decision sheet at the front of every item: what is being asked, what the alternatives were, what could go wrong, what the executive recommends. Everything else is an appendix. This single change does more for board debate than any amount of behavioural coaching.
Ask for the dissent explicitly. Not “any questions?”, which invites silence. Try “what would have to be true for this to be the wrong decision?” and then go round the table. Nobody gets to pass.
Reverse the order. Newest and least senior first, chair last. If you speak first you have not run a discussion, you have issued an instruction and collected agreement.
Hold an executive session every meeting. Twenty minutes, directors only, scheduled as a matter of course. A session held only when there is a problem announces that there is a problem; a session held every time is simply how the board works, and it is where the car park conversation goes when you give it somewhere legitimate to live.
Talk to each director between meetings. Fifteen minutes, one to one. You will hear the reservation three weeks before it would have reached the car park, and you can arrange for it to be aired by the person who holds it.
Minute the dissent. Not to apportion blame later, but because a board that records “two directors questioned the assumptions on X” is a board where questioning the assumptions is a normal and safe thing to do.
How to know whether you have this problem
You will not find it in the board evaluation, because the same politeness that suppresses the dissent will sand down the survey. Three better tests. Ask yourself when a board resolution was last carried other than unanimously. Ask whether any director has changed their stated position during a meeting in the past year. And notice who talks to whom on the way out — if the same two people always leave together, they are holding a meeting you are not invited to.
The measure of a board is not whether it agrees. It is where the disagreement happens.
· William (Bill) Best is the founder of Garrett Lane Advisors. .
Insights · Turnaround · September 2026 · 8 min read
Digitising a business is an operating decision, not an IT one
A million-dollar platform investment is easy to defend once assets have gone from $675 million to $4.25 billion. It is very hard to defend in the week you propose it.
When I took on the operations of an ailing wealth and investment management business, the problem was not really the operations. It was that nobody could see them. The management information was too thin to run the company on: we could tell you what had happened by the time the quarter closed, and by then it had already happened.
What we did about it was, on paper, a technology project — a million dollars into a platform that digitised the business end to end, from asset management through to fee generation. What it actually was is an operating decision that happened to involve software. The distinction is not semantic. It determines who sponsors the work, how it is scoped, what you measure, and whether it delivers anything at all.
Why these projects fail
Most failed digitisation programmes I have seen failed the same way. The business handed the problem to technology, technology delivered exactly what was asked for, and the business did not change.
You can spot it in the success criteria. If the project is judged on delivered to time, delivered to budget and went live, it is an IT project and it will produce an IT outcome: a system, running, that people work around. Nobody lies about this. Everyone does what they were measured on.
The other failure is subtler and more expensive. You digitise the process you already have. If that process is bad — and in a business that needs turning round, it is — you have not fixed anything. You have made it fast and wrong, and you have hard-coded it so that fixing it later costs three times as much.
Four rules I would apply again
The sponsor is the operator. The chief operating officer, the chief executive, whoever actually owns the P&L. Not the CTO, who should be building it rather than justifying it. If the person defending the investment at the board cannot describe the business outcome without using the product name, you have the wrong sponsor.
Start from the question you cannot answer. Not from the system you want. Ours was simple enough to say out loud: what is actually happening in this business between quarter ends, by asset, by adviser, by fee? Write your question down before you look at a single vendor. It becomes the specification, and it becomes the test.
Sequence around the money. The revenue chain first — assets in, activity, fees out. Everything else waits. This is unpopular with everyone whose function is not the revenue chain, and it is the reason the investment can be defended at the halfway point, which is when it will need defending.
Fix the process before you buy the platform. Every one of these programmes is an opportunity to retire a decade of accumulated exceptions, and the opportunity closes the day configuration starts.
Making the case to a board
The difficulty is that the return is real and the timing is unprovable. You are asking for a large cheque against a benefit that arrives in eighteen months, in a business that is currently underperforming, which is precisely when a board is least inclined to write large cheques.
Three things helped. First, framing the investment against the cost of the current state rather than the promise of the future one — not “this will grow assets”, which nobody can promise, but “this is what we currently spend producing numbers we do not trust”. Second, being explicit that the platform was necessary and not sufficient: it would make growth possible, and people would still have to go and do it. Third — and this is the one most people skip — agreeing in advance what we would report every month while the thing was unproven.
That last point matters more than the pitch. A board’s confidence in an eighteen-month investment is not built at approval. It is built in months four through nine, when there is nothing to show and you are still turning up with something honest to say.
What to measure while it is unproven
Not milestones. Milestones measure the project, and the board is not buying a project.
At ninety days: is the revenue chain data complete and reconciled, and how far behind real time is it? At six months: how many of the manual processes it was meant to retire have actually been retired — a number that is almost always lower than the plan, and the gap is the honest status report. At a year: can a manager answer a question about their own part of the business without asking anyone for a report?
That last test is the one I care about. The technology was never the achievement. The achievement was that we could finally see the business — and once you can see it, the decisions that had been guesses become ordinary management.
· William (Bill) Best is the founder of Garrett Lane Advisors. .
Insights · Succession · September 2026 · 7 min read
Succession is a five-year decision made in five weeks
Most boards know the date their chief executive will leave years in advance, and still run the process as an emergency.
Chief executive succession is the only decision a board makes that is absolutely guaranteed to arrive. Every other item on the agenda is contingent. This one is arithmetic — the incumbent will leave, by choice, by health, by performance or by age, and in most cases the board has a rough idea of when.
And yet the process usually starts far too late, compresses into a handful of weeks, and produces a decision that the board would not recognise as its normal standard of work if it were buying a business rather than choosing the person who will run one.
Why boards defer it
Not incompetence. Three quite human reasons.
Naming a successor starts a clock, and everyone in the room knows it. The chief executive hears “we are planning for after you”, the successor hears “your turn is coming”, and the chair, who has to work with both of them next Tuesday, decides the conversation can wait a quarter. It waits several quarters.
There is also the awkwardness that the person best placed to judge internal candidates is the one being replaced, and asking a chief executive to assess their own replacement is asking a great deal of anybody. And there is simple crowding out: the committee has a remuneration cycle, a director search, an evaluation to commission. Succession has no deadline, so it never wins.
The three things to have in place first
Long before any conversation about names, a nominating committee should have three things. Each one is cheap. Each one is almost always missing.
A written specification of the next chief executive — not the current one. The question is not “who could replace the CEO?” but “what does the strategy we have just approved require of whoever leads it for the next five years?” These give different answers, and the second one is the right question. If the plan is international expansion and the incumbent is a domestic operator, the specification should say so, in writing, while everyone is calm.
Two internal candidates being developed on purpose. Not identified — developed. Real P&L accountability, exposure to the board rather than one presentation a year, a stretch assignment that could plausibly fail, and someone honest telling them where they fall short of the specification. If your internal bench is “strong” but has never presented bad news to the board unaccompanied, you do not have a bench.
An emergency successor, named today. This is a different question from the planned one, and it must be answered separately. If the chief executive were unavailable tomorrow morning, who signs, who speaks to the market, who runs the company for ninety days? Decide it, write it down, review it annually. Most boards think they have this and have not tested it against an actual calendar.
Internal or external
The temptation is to decide this first, because it feels like the big question. It is not. Run the specification first, then test both markets properly, and let the answer come out of the comparison rather than out of a prior conviction.
What matters more is what happens to the internal candidates who do not get it. A badly run process costs you the successor and both runners-up within a year, which converts a succession into a restructuring. Talk to them early about how the process will work, tell them the truth about where they stand while there is still time to act on it, and decide in advance what you will offer them the day the announcement goes out.
The incumbent’s role
Involved, consulted, and not deciding. A chief executive’s view of the internal candidates is valuable data — nobody else has watched them under pressure for five years — and is also the view most likely to favour the person who most resembles the incumbent. Take it as evidence, weight it accordingly, and make sure the committee has its own independent view of every candidate.
It also helps enormously to agree what the outgoing chief executive does afterwards, early and in writing. Ambiguity about a continuing role is the single most reliable way to undermine a successor in their first year.
Working back from the date
Twenty-four months out, agree the specification against the strategy. Eighteen months, honest assessment of each internal candidate against it, and the development plan that follows. Twelve months, test the external market — properly, not as a formality. Six months, decide. Three months, announce and hand over. Anything shorter is not a process, it is a reaction with a process-shaped press release attached.
None of this requires the incumbent to be leaving. That is exactly the point. The only time to run a succession process calmly is when nobody needs one.
· William (Bill) Best is the founder of Garrett Lane Advisors. .
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