What kind of help does my business actually need?
I once went down a ridiculous rabbit hole with a colleague about all the different kinds of help businesses can hire: different flavours of COO, Chief of Staff, consultants, coaches, advisors, agencies and the ominous “Special Projects.” I have also sat on several sides of the decision inside companies as an executive and transformation leader, and outside them as an advisor, consultant and fractional operator. The titles are considerably less useful than people pretend.
So forget what the world says you “should” hire for a minute. Which sentence sounds most like your actual problem?
Choose your own adventure
Describe the problem before choosing the title
A private decision worksheet to clarify what needs to change and whether you need perspective, expertise, ownership, coordination or capacity.
1 — Advisor
An advisor is an experienced thinking partner. You still own the decision; they bring perspective, pattern recognition and challenge. Useful when the problem is messy and the decision matters. Watch for an advisor who needs to manufacture a giant project to justify being there.
YOUR ENDING: You leave with a decision you understand and still own. Sometimes the most valuable outcome is deciding not to launch the expensive project everyone had started convincing themselves was necessary.
Back to the choices ↑2 — Consultant
A consultant investigates or solves a defined problem. They may assess, design, recommend, build a roadmap or help implement it. Useful when there is a piece of work that needs expertise and an answer. Watch for a beautiful deck that leaves your team admiring the problem in considerably nicer fonts.
YOUR ENDING: You should finish with the problem understood and a clear answer about what changes next. If all you have is a better-looking description of the problem, you bought a deck.
Back to the choices ↑3 — Fractional executive
A fractional executive steps inside the business and owns a meaningful area for an agreed amount of time. They make decisions, lead people where appropriate and carry responsibility for results. Useful when you need senior ownership but not a full-time executive. Watch for paying executive rates for someone who mostly attends meetings and gives advice.
YOUR ENDING: The area now has senior ownership without creating a permanent executive role before the business needs one. The test is whether decisions and results genuinely move without routing back through you.
Back to the choices ↑4 — Full-time executive
A full-time executive owns an enduring part of the company every day. The role should have enough authority, accountability and permanent work to justify the seat. Watch for a grand title attached to a vague collection of founder leftovers.
YOUR ENDING: This should remove an enduring piece of the business from your personal workload, not add another senior person for you to coordinate. If the role cannot be described clearly before hiring, the title will not fix it.
Back to the choices ↑5 — Chief of Staff
A strong Chief of Staff is a force multiplier around an executive: preparing decisions, coordinating important work, driving follow-through and making sure things do not quietly die between meetings. Useful when the executive has become the coordination point for too much important work.
But the role can cut both ways. A great Chief of Staff can accelerate the best parts of a CEO or enable the worst. If the CEO is the bottleneck, adding someone whose job is to help them manage the bottleneck can make the whole thing more efficient without actually fixing it.
YOUR ENDING: A good Chief of Staff gives the executive back attention: fewer loose ends, better prepared decisions and less time being the human connection point between everything. Just be careful you haven’t hired someone to make founder dependency run more efficiently.
Back to the choices ↑6 — Specialist / agency
Sometimes you need deep capability in one discipline (technology, legal, finance, recruiting, design, marketing or another specialty) without building it permanently inside the company. Watch for outsourcing something the business actually needs to learn to do itself.
YOUR ENDING: You get depth you do not need to build permanently. Be clear about what expertise can leave when the engagement ends and what the business needs to retain.
Back to the choices ↑7 — Contract / project support
Sometimes there is no strategic mystery. The plan is clear and your team is simply full. Contract or project support gives you experienced capacity without pretending the problem is more complicated than it is.
YOUR ENDING: Nothing gets reinvented. You add capable hands, finish the work and stop paying for capacity when you no longer need it. Wild concept.
Back to the choices ↑8 — Oh dear
You chose “We need a results-driven transformation leader to unlock cross-functional synergies, break down silos, drive Agile ways of working and accelerate enterprise value creation.”
You have fallen through a hole in the universe.
Go back to the beginning and tell me what is actually happening. No job titles. No transformation language. No synergies.
Back to the choices ↑If you can describe the problem in normal English, you’re much closer to figuring out who you actually need.
Let’s talk about the help you actually need
Start with a conversation about the problem, the work and the kind of help that would provide value.
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