The short version: A productivity tool is worth using if it saves you more time than it costs you to set up, learn, and maintain, and if you’d notice the pain of losing it within a week. Everything else is a feature list dressed up as a solution. Most tools fail this test not because they’re badly built, but because the problem they’re solving was never really a tool problem in the first place.
The £149 lesson that changed how I buy software
In 2019 I bought a lifetime deal on a task management app called Flow. £149, one-off payment, no ongoing subscription, sounded brilliant. It had Gantt charts, recurring tasks, a nice calendar view, integrations with everything I used at the time. I set it up on a Sunday evening, imported my task list, colour-coded my projects, felt very organised indeed.
I used it for six weeks. Then I opened it once a fortnight to feel guilty. Then I stopped opening it at all.
The tool wasn’t bad. It did exactly what it said it would do. The problem was that I never had a task management problem. I had a “too many half-finished commitments and no clear priority” problem, and no amount of colour-coding a list fixes that. Flow made my mess look tidier. It didn’t make me do less or decide better. That’s the trap, and it’s one I’ve fallen into more than once since, with a habit tracker, two separate CRMs, and a note-taking app I paid annually for and opened maybe four times.
If you want a proper method for working out which tools deserve a place in your day before you hand over your card details, I wrote a longer piece on how to find productivity tools that really save you time, and the short version of it is this: you test for the problem, not the software.
The question nobody asks before they buy
Here’s the uncomfortable bit. Most people don’t buy productivity tools to solve a workflow problem. They buy them because using a new tool feels like progress, and it’s easier to spend twenty minutes setting up a system than to spend twenty minutes doing the actual boring task the system was meant to help with.
I’ve done client audits where the business owner has four project management tools running at once, none of them fully used, all of them justified with some version of “well, this one’s better for the marketing team.” That’s not a tooling problem. That’s avoidance wearing a productivity costume. If you notice you’re more excited about building the perfect system than doing the work the system organises, that’s worth sitting with before you buy anything else.
What “worth using” looks like in numbers
I judge a tool on one rough calculation: time saved per week minus time spent maintaining it, over a three month period. If that number isn’t clearly positive by week four, the tool goes.
Some real examples from my own stack:
- Otter.ai for transcribing client calls: saves me roughly 90 minutes a week I’d otherwise spend writing notes from memory. Setup took ten minutes. Still using it four years on.
- Calendly for booking calls: saves maybe 30 minutes a week in back and forth emails, but the real win is fewer missed meetings, which used to cost me a full hour every time it happened.
- A social media scheduler I won’t name that I paid for annually and used for one launch: cost £240 a year, saved me maybe two hours across the whole twelve months because I kept reverting to posting manually. Cancelled.
Small tools that solve one clear, recurring problem beat big platforms that promise to solve everything. The 30 tools I’ve tested and kept using long term have one thing in common: they each do a single job I couldn’t be bothered to do manually, and they do it without me having to think about them. If you want a list of tools with no catch, no trial that expires, no upsell three months in, have a look at my roundup of 30 free business tools. Free doesn’t mean worse. It just means fewer people trying to upsell you.
Seven signs a tool has earned its place
After years of buying, testing, and quietly cancelling software, here’s what I’ve noticed separates the keepers from the abandoned:
- You’d feel the loss within a week if it disappeared, not just annoyance, an actual gap in how you work.
- It took under an hour to get real value from it, not just set it up, get value from it.
- You use it without opening a tutorial, a help doc, or asking someone else how it works.
- It replaced a task you were doing badly or reluctantly, not one you were doing fine.
- You haven’t had to build a workaround for something it should just do.
- Nobody on your team has quietly gone back to doing it the old way.
- You’d pay for it again at full price, not just because you already sunk the cost.
That last one is the honest test. Sunk cost keeps more dead software alive than any marketing team could manage on their own.
The 20-minute audit I run on my own stack twice a year
Twice a year, usually January and July, I go through every tool I’m paying for and answer four questions for each one, out loud, timed at roughly two to three minutes per tool.
- When did I last open this, and what did I do in it?
- If it vanished tomorrow, what would I lose?
- What’s it costing me a month, in money and in the time it takes to maintain?
- Would I sign up for this today, knowing what I know now, if I saw it for the first time?
Last July this exercise found me three subscriptions totalling £67 a month for tools I hadn’t opened in over eight weeks. That’s £804 a year for software doing nothing but sitting there. It also confirmed that a £12 a month AI writing assistant was earning its keep because I used it four or five times a week and it consistently cut a 40 minute drafting task down to 15.
This is worth doing even if you think your stack is lean. I’ve never run this audit on my own business or a client’s and come out with zero to cut.
Why AI tools make this harder to judge, not easier
The last two years have thrown a new complication into all this. Everyone’s adding AI features to everything, and half the time it’s a genuine improvement and half the time it’s a chatbot bolted on to justify a price increase. The way I test AI tools now is the same way I’d test a new hire’s first draft: does the output need heavy editing, or is it close enough to use with small tweaks? If I’m rewriting most of what an AI tool gives me, it’s not saving me time, it’s just moving the work from “doing it” to “fixing it,” which is often slower.
The same test applies to the prompts you build for these tools, by the way. Not every prompt deserves to be saved and reused. I’ve written before about what makes a ChatGPT prompt worth saving, and the criteria overlap almost exactly with what makes a tool worth using: does it save real time on something you do often, and does it work without you needing to rebuild it from scratch every time.
The habit question underneath all of this
Here’s something I’ve had to accept the hard way. No tool fixes a habit problem. If you don’t have a habit of reviewing your priorities, no priority app will build one for you. If you don’t have a habit of checking your numbers, no dashboard will make you look at it. The tool can make the good habit easier once you already have it. It rarely creates the habit from nothing.
I keep a shortlist of habits I rely on, most of which need no software at all, in my piece on 25 productivity habits for entrepreneurs. Reading it back after years of testing software, the habits have outlasted almost every tool I’ve bought to support them.
When the answer isn’t a new tool at all
Sometimes the honest answer to “what’s the best productivity tool for this” is that you don’t need one. If a task happens once a month, a spreadsheet beats a subscription. If a process only exists because three people in your team do it slightly differently, no tool fixes that until the process itself is fixed. I’ve watched businesses spend thousands rolling out project management software to paper over a decision-making problem that no software touches, because the real issue was that nobody was clearly responsible for signing things off.
Buy the tool once the process is clear enough that the tool has something specific to hold. Buy it before that, and you’re just automating confusion faster.
Frequently asked questions
How do I know if a productivity tool is saving me time or just feels like it is?
Track it for two weeks. Note how long a task took before the tool and how long it takes now, including setup and any fiddling. If the maths isn’t clearly in your favour by week two, it’s the feeling of productivity, not the fact of it.
What’s the biggest mistake people make when choosing a productivity tool?
Buying based on features rather than on a specific, recurring problem they already have. A long feature list is a sign the tool is trying to be everything to everyone, which usually means it does most things adequately and nothing particularly well.
How many productivity tools should a small business use?
Fewer than you think. Most small teams I’ve worked with run comfortably on five to eight core tools once the overlap and abandoned trials are stripped out, down from fifteen or twenty they were quietly paying for.
Should I cancel a tool I’ve paid for annually if I’m not using it?
Yes. The money’s spent either way. Keeping a subscription active because you already paid for the year is sunk cost thinking, and it usually costs you more in mental clutter than the refund you’ll never get would have been worth.
