Most changes at an accounting firm start in a partner meeting. Someone sees a demo, the numbers look good, the contract gets signed, and the team finds out when a training invite shows up in their inbox.
By then, the most important decisions have already been made. The people who will use the new tool every day had no say in which problem it was supposed to solve or how success would be measured.
Gartner has put a number on what it costs to leave your team out of change management decisions. In a July 2025 survey of 313 senior leaders, organizations that regularly adapted their change plans based on employee responses were four times more likely to achieve change success. That is a large return on a few honest conversations.
With 2027 planning underway and new AI tools arriving daily, now is a good time to ask your team before you announce a new tool. These five questions will surface the problems that would otherwise show up three months after rollout.
1. What does a good day at work look like for you right now?
I’d start with what’s working. This question tells you which parts of the job give people energy, and those are the parts you want to protect as everything around them changes.
If a senior associate lights up talking about walking a client through a cash flow problem, automating the prep work around those conversations will feel like a gift to them. If your plan changes the client conversation itself, you’ll know to expect resistance before you spend a dollar on implementation.
2. Where do you lose the most time?
The vendor demo shows you where time could be saved. Your team can tell you where it actually goes.
The answers often point to a process problem: a handoff nobody owns, a client who always sends documents late, or a review step that happens twice because two people thought it was their job. A new tool won’t fix any of those, and it can make the wrong process run faster. Aim the change at the friction your people describe, and you’ll get adoption without having to push for it.
3. What worries you about this change?
Ask it directly, and resist the urge to answer every concern on the spot. People will tell you what worries them only if they believe you want to hear it.
Gartner warns that employees sometimes perform change, attending the training and saying the right things, without actually adopting it. If enthusiasm is the only safe answer in the room, you’ll get enthusiasm in the meeting and old habits at the desk. The worries you hear before rollout are far cheaper to address than the workarounds you discover after it.
4. What would tell you this is working by the end of the first month?
Most firms define success at the finish line, with full adoption, hours saved and a faster close. Those goals are months away, and people lose momentum long before they get there.
Gartner advises leaders to focus on helping employees make progress during the change. Ask your team to name the early markers: the first client file finished without a workaround, or the first week nobody exported the output to a spreadsheet to double-check it. When the team helps write the definition of success, they have a reason to watch for it.
5. Who should we be asking that we haven’t asked yet?
Change plans tend to be built from the opinions of whoever is already in the room. The admin who handles client onboarding, the staff accountant who fields every exception and the remote team member who rarely speaks up in meetings often know exactly why the current process looks the way it does.
This question invites your team to bring those people in. It’s also the fastest way to find the person who knows about the workaround nobody documented.
What do you do with the answers?
Write them down. Then go back to your team and tell them what changed because of what they said, whether that’s the timeline that moved, the feature you turned off or the task you took off someone’s list. Closing that loop is what makes people willing to answer honestly the next time you ask. If an answer doesn’t change the plan, say that too and explain why. People can accept a decision they disagree with much more easily than one that seems to have ignored them.
At the end of the first month, check back using the markers from question four. Ask what’s working, what isn’t and what needs to shift, and then make the adjustments.
Before your next rollout, block an hour with your team before the training invite goes out. Ask these five questions and listen to the whole answer. It will be the most valuable hour of the entire implementation.
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