The Step In The Middle

I've had more than my fair share of frustration this week. The more time I spend in Claude (Claude Code, Cowork, or just chat), and the more time I spend with skills, the more frustrated I get. Not with the results I'm getting, but with the repeatability. Any time I don't keep my knowledge documentation up to date, any time I forget to commence my work and chats in the right projects, it makes something harder to find later on because I don't have a good process keeping me safe. I usually don't find out there's a problem until I put something down for long enough that I've forgotten what the process looks like. The tool is great. It's phenomenal. But the connection between me and the tool sometimes feels broken, and that's the essence of what I want to talk about today, because it's the problem of process.

We adopt the tool, we get excited about what it can do, and we never quite get around to the work that would make it of use in a repeatable, durable way for us. The same is true with advisory work. We define the problem well enough. We know what's not working, and we can name the gaps. But then we go shopping, and sometimes it's in the name of helping define the options. We end up comparing features, sifting through demos, weighing up benefits, and then we pick a tool.

That process step in the middle – between understanding the problem and comparing the tools – gets missed, or we try to retrofit it to our business. And in doing so, we get sucked into the features of the tools, because every feature suddenly looks like value. Every demo looks impressive. The comparison becomes about which tool has the most of everything rather than which tool fits our way of operating.

If you don't know where you're going, any road will get you there.

The last newsletter issue was about the seven questions we ask of an AI tool once we've decided AI is the right move. This issue is the work upstream of that. How to evaluate process fit before you've adopted anything that touches advisory work – your reporting cadence, your client conversations, your analysis layer, the way clients experience your insight. What to ask yourself, what to look for, and what to do when the honest answer is that this tool doesn't fit, even though it looked promising.

Lests start with with what fit-for-purpose actually means. For advisory work, in my opinion, fit isn't a property of the tool. It's a property of how the tool sits inside the way you actually deliver insight to clients.

A reporting tool can produce beautiful outputs and miss the things you actually talk about in client meetings. An AI assistant can write polished narrative and lose the nuance that turns a finding into a conversation. The fit is in the use, not the spec.

The work is to define what fit-for-purpose looks like for you, in your process, with your team, with your clients – before you've looked at any tool. Once you've done that, every feature becomes legible. Features that serve the fit are valuable; features that don't are noise.

The cleanest way to ask the fit question is also the most honest one. What does satisfaction look like – for the team running this process, and for the clients receiving what comes out of it?

Satisfaction sounds soft in a business context. It isn't. Satisfaction is how humans actually evaluate the things they do every day. We don't run stopwatches on our work; we feel whether something is right or wrong, whether it's purposeful or not. We do what we feel is good for us. We resist what doesn't. That isn't sentimentality. It's how humans work.

The criterion question has three honest sub-questions, all of them about how the work feels when you're inside it.

When I'm in this work, does the process support me, or am I working around it? There's a difference between a tool you reach for without thinking and one you brace for every time you open it. That difference, felt honestly, is the answer.

Does the work feel purposeful? Sharper client conversations and clearer invoices feel purposeful. Logging time because the system demands it, when nobody ever looks at the data, feels like a tax.

Does this feel aligned with what we're trying to be – for ourselves, our business, our clients? Not do our stated values match this tool but the felt version: when I use this, does it feel like the kind of practice I'm trying to run, or does it feel like I'm becoming something I didn't choose?

When we took over the bookkeeping firm in 2021, we inherited a ClickUp rollout that was halfway done. The need was real – important deadlines being missed, structural things falling through the cracks. What we learned wasn't really about features. It was about helping each member of the team understand the process they were now following, and helping them believe – not abstractly, but in their bones – that following it would keep them safe and benefit them personally, not just serve the company. The work was compliance work; the discipline of adoption is the same in advisory.

ClickUp can do almost nothing, or it can do almost everything. We didn't pick the maximum version. We picked the version that fit. That distinction – between what the tool is capable of and what amount of tool the work actually needs – matters more than features ever will.

Once you've named what satisfaction looks like, there's a quieter question to ask: what's currently working that you don't want to disturb?

Adoption is never a fresh start. You're adding something to a working system. In an advisory practice, the things you won't break are usually about the relationship. The cadence of the monthly conversation a client has come to expect. The format of how findings get delivered. The shared mental model between you and the client about what good looks like for their business. These are sources of felt safety and felt rhythm. Disturb them carelessly and you don't just lose efficiency, you lose the trust that the change isn't being done to the client.

The honest test: what would the team mourn if it went away? What would the client notice has changed for the worse, even if they couldn't quite name it? If the new tool requires either, you have a fit problem before you've started.

The question most practices forget to ask is what their tool decision does to the client.

Last week's issue named the customer dimension as one of the prior questions. This week's version is deeper. In advisory work, the client doesn't experience your tool through reports. They experience it through the quality of the conversation you have with them about their numbers. If the new tool changes how you prep for client meetings, what you can see at a glance, how quickly you can answer a follow-up question, then the client experiences a different advisor – even if nothing about your relationship has changed in your mind.

So the fit question is two-sided. What does satisfaction look like for our team? And separately: what does the client experience of working with us look like, before and after the change? Both have to clear the bar.

Sometimes the work above produces an answer you didn't go in expecting. The problem is real, the tool is capable, the demo was impressive, and the honest answer is still that this tool doesn't fit. Not because anything is wrong with it. Because the fit isn't there in your process, with your team, for your clients.

That's hard to land on after you've invested in evaluating. The temptation is to find a reason to proceed anyway. To convince yourself the misalignment is small, that it'll be fine once people get used to it, that the discomfort is just change-resistance and not a real signal. Sometimes it is. Often it isn't.

The discipline is to say the answer out loud anyway. We've looked at this carefully, it would solve the problem we have, and it isn't the right fit for how we work. Walk it back. Keep looking, or accept that the current state is closer to satisfactory than you thought. Either is a better outcome than forcing a tool that doesn't fit and watching the practice contort itself around it for the next two years.

In advisory work, process fit is the thing that decides whether the people who'll have to live with your tool choice – your team, and your clients – feel that doing so is good for them. If you can't answer that with specificity, before you've adopted anything, you don't have an adoption plan. You have a procurement decision.

Notion is where the work instructions, SOPs, and process documentation live for our practice. Client handover notes, the structure for how we run a monthly close, the templates we use for variance commentary, the prompts and patterns I keep referring back to when I'm working with AI. It's the answer to where do I find the thing I did successfully last time.

The tension worth naming honestly: Notion is enormously flexible, which is a feature and a problem. It has no opinions about how you should use it, which means you have to bring all the structure yourself. Adopting Notion without first deciding what kind of structure you actually want from it is the small-scale version of the same trap this issue is about.

Notion has been adding AI features at speed. What I use it for sits underneath that – the structured layer that holds the work, regardless of what AI does or doesn't get pointed at it.

There's a generous free tier. notion.com if you want to look.

I started this issue with a confession about my own AI work, and the reason it's relevant is that none of this is theoretical for me. The discipline of getting clear on what good looks like before reaching for the next tool is the work I'm trying to do better in our own practice, week by week. The connection between me and the tools I use is something I'm actively trying to repair – with structure, with process, with the patience to do the upstream work that makes the rest of it actually hold together. I'd guess most of you are in some version of that work too. That's the conversation I want this newsletter to be part of.

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Know someone navigating the compliance-to-advisory transition? Forward this email — or better yet, send them to baifokal.beehiiv.com to subscribe.get "good meeting, thanks" as they walk out the door, that one's for you. Hit reply and tell me about it — I'm genuinely curious how many of us have had that exact experience.