A Senior Advisor In Your Corner.

Ongoing one-to-one work for established business owners who want depth on what's actually on their mind. Monthly, in person near Harrogate or on Zoom.

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What This Actually Is.

A single, ongoing relationship with someone who's done the job and who'll engage seriously with whatever you bring.

Monthly working sessions on the things that actually matter, a shorter catch-up partway between, and direct contact when something can't wait. In person if you're close to Harrogate, on Zoom if you're not.

The work itself is whatever's most important to you right now and over time. A decision you've been turning over for months. A part of the business that isn't working and you can't see why. A person you can't quite get right with. Where the business actually needs to be in three years, and what has to change for it to get there. These aren't easy conversations and they're not meant to be.

What I bring is experience, honest challenge and the questions you won't put to yourself. I push you where pushing is useful. Between sessions, I hold you to what you said you'd do. I won't tell you what to do. The decisions you make are yours. My job is to make sure you've thought them through properly, with someone who's been in your chair.

Who’s It For.

Owners of established businesses with a team around them. People who've been doing this long enough to know what they're good at and what they're not.

Coaching is the right call if you want depth on what's actually going on, rather than the broader thinking of a peer group. Some clients have specific challenges they want to work through over a period. Others want a senior, ongoing relationship with someone outside the business who knows them and knows the company. Either way, the value is in the depth of a single conversation, sustained over time.

Three things matter more than the numbers.

You're willing to be honest. About the business, about your decisions, about yourself. The work doesn't move if you're protecting your position or unwilling to look at the harder questions honestly.

You care about the people around you. Your team, your customers, your suppliers, the community the business sits in. Straywise isn't for owners looking for tactics to extract more from the people they depend on.

You take your own decisions. I'll bring challenge, perspective and experience. What I won't give you is the answer. You listen, you weigh it, and you decide.

How It Works.

The work is confidential. What's said between us stays between us.

There's no fixed contract. You start, you pay monthly, and you give a month's notice if it stops being right for you. Most clients work with me for years because the depth of the work compounds over time, but the door is never locked.

I take a small number of one-to-one clients alongside The Stray Board, deliberately, so that everyone gets the attention the work needs. When I'm full, I'm full. I'll tell you straight if I am.

The geography is Harrogate, Leeds, York and the surrounding area for in-person work. Beyond that, we work on Zoom.

Everything we do together runs through a proper coaching platform. One place for session notes, actions, plans, and the exchanges between us. Whatever we build together stays yours. If you ever walk away, you keep access to it all for as long as you want it.

Who Is Coaching You?

I'm Andrew Jackson. Twenty years in business that took me from a mailroom to chief executive of a £300m global company. The last ten coaching owners of established businesses, mostly in Yorkshire.

I've also been a part-owner in two SMEs, one of which I helped build, grow and sell. So when I'm in your corner I know what running an SME is actually like, not just what it's supposed to look like from the outside. The pressure, the loneliness, the moments when it's brilliant and the moments when it isn't.

I do this work because these are the conversations I wish I'd had earlier in my own career. The right time to have them is usually a couple of years before you think you need to.

Read More About Andrew

What My Clients Have Said.

  • "Andrew was a brilliant support throughout our Management Buy Out. A calm, steady presence during what was inevitably a complex and demanding process. When things felt messy or unclear, he had an uncanny ability to help me cut through the noise and get back to what actually mattered. Three and a half years later, I'm still working with him. What I appreciate most is that he doesn't default to telling you what to do. Sometimes he gently helps you see that you already know the answer. Other times he asks a question that completely reframes the issue. Either way, you walk away clearer, steadier and more capable than when you sat down."

    Georgina Parkin, Owner and Managing Director, Truth Legal

  • "I first got to know Andrew through a peer board he chaired, and we've worked together one-to-one ever since. What stood out from the start was how clear-headed he is. Whatever you bring to him, he has a way of narrowing it down to the two or three things that will actually move the business forward. He's also not a high-level sounding board. He got into the detail, sat in management meetings with me, helped reshape how we approached proposals and applications, and was a real part of how we ended up selling the business five years in. That outcome was life changing for my family, and Andrew deserves a lot of credit for making it happen."

    Gary Thompson, Founder, Smartflow Couplings

  • "Andrew's entrepreneurial character and ability to connect the dots, allows him to guide you with visible and sustainable results."

    Riccardo Tonelli

  • "Clarity, Wisdom & Composure, Andrew's guidance has been invaluable"

    Andrew Gray

Frequently Asked Questions

  • Fees are monthly and we discuss them properly in the discovery conversation. They sit in the range you'd expect for serious, ongoing work with someone at this level of experience, and they're the same for every client. If cost is a deal-breaker you'll know quickly. If it isn't, we'll talk about value.

  • The Board is six owners in a room together once a month, with you as one voice among them. Coaching is one ongoing relationship with me, on the things specific to your business and your life. Some clients are on the Board and have coaching as well. Others want one or the other. Which is right for you usually becomes clear in the discovery conversation.

  • Years, in most cases. Coaching is built for depth and depth takes time. That said, the work doesn't run on a fixed clock. Some clients stay for two or three years and step away naturally. Others have been working with me for the best part of a decade. The right length is whatever serves you best.

  • You give a month's notice and we stop. If something hasn't been working, I'd want to know honestly so I can learn from it, but that's a conversation, not a condition. The door is never locked.

If This Sounds Like The Work You Want.

The next step is a conversation. No pitch, no script. Twenty or thirty minutes on Zoom to talk about where you are, what you're looking for, and whether ongoing coaching is the right fit. If it is, we book a longer meeting to go deeper. If it isn't, I'll say so.

Contact Andrew

Not Sure Yet?

Take the Business Freedom Scorecard. Twenty-one short questions across five areas of your business, ten minutes to complete, an honest read on where you actually sit. It's free, and it'll tell you more about what you're carrying than you might expect.Take the scorecard here.