I have learned to be careful about who I let influence an important decision.
Advice is everywhere. It arrives in meetings, over coffee, in online comments and sometimes from people who have never faced the problem they are confidently explaining. Most of it is well intended. That does not make it useful.
Whenever I am trying to move towards a new goal, I pay closest attention to people who have already navigated similar terrain. They do not need to have followed my exact route. They do need to understand the trade-offs, uncertainty and consequences that come with it.
Experience changes the question
Someone looking in from the outside often focuses on what appears sensible. Someone who has done the work tends to ask different questions.
They ask what I am prepared to stop doing. They ask what happens when the early excitement disappears. They ask whether the opportunity still makes sense after allowing for support, cash flow, staff capacity and the cost of distraction.
That difference matters.
I see this regularly with AI and Microsoft 365 Copilot. A business owner may hear broad advice to “roll out AI” because competitors are doing it. The more useful conversation usually comes from someone who has actually worked through adoption inside a real organisation. They know that buying licences is the easy part. Information quality, permissions, staff confidence, workflow design and management expectations are where the real work begins.
The lesson is simple. I want guidance shaped by consequences, not just opinions.
Look for relevant scars, not impressive titles
I do not assume the most senior person has the most relevant answer. Position and experience are not the same thing.
If I am considering a new managed service, I want to speak with someone who has priced it, sold it, supported it and dealt with the awkward client conversation when delivery did not match expectations. If I am changing how my team uses Copilot, I want to hear from someone who has tested it in Outlook, reviewed the drafts, discovered where the underlying information was weak and adjusted the process.
That person can tell me where the friction actually appears.
Copilot can also help me prepare for that conversation. Before asking for advice, I can use it to summarise relevant emails, meeting notes and documents I already have access to. That gives me a clearer picture of my own situation. I can then ask a specific question instead of handing someone a vague ambition and expecting a useful answer. Microsoft confirms that Copilot can ground responses in accessible work data such as emails, files, chats and meetings, while respecting the user’s existing permissions. [support.mi…rosoft.com], [support.mi…rosoft.com]
Good advice improves when I bring good context.
Borrow judgement, not instructions
Even experienced people can only speak from their circumstances. Their market, timing, finances, risk tolerance and responsibilities may be different from mine. I am not looking for a set of instructions to follow without thinking.
I am looking for tested judgement.
The best advisers help me see what I have overlooked. They explain why a choice worked, what nearly broke, and what they would approach differently now. They do not pretend their path is a template. They help me make a better decision about mine.
I also pay attention to whether their current position matches the destination I actually want. Achievement can look impressive from a distance while carrying costs I would never choose. The outcome matters, but so does the way it was achieved.
I will listen widely. Different perspectives can expose blind spots. But when a decision has real weight, I give greater value to the voices that come with lived experience.
Opinions describe the road. Experience remembers the potholes.
