Ask each person what they'd want off their plate

Instead of guessing which tasks to automate first, simply ask each person on the team what part of their job they'd most like to hand off if they could. I ask this question before I ever suggest a tool, because I've learned my own guess about someone's biggest headache is usually wrong. People know their own frustrations better than any outside observer ever could, and the answers you get are usually more specific and useful than anything a general planning session would produce. This approach also makes the rollout feel like it's being built with the team instead of done to them, which matters more for lasting adoption than almost anything else you could do. Some answers will overlap, pointing you straight to the task most worth solving first, while others will surprise you and reveal a headache you never knew existed. Either way, you end up with a far better starting list than you'd have picked alone.

Try this today: ask everyone on your team this week what one task they'd most like to hand off, and use the most common answer as your next target.