Developing Expertise at Work: A Guide

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Every company has a shortage of experts. The world inside and outside every organization is constantly changing, and even someone who has solved a problem before hasn’t solved it in the current context. In a fast-paced company, this creates opportunities for people who are willing to put in the effort to learn and adapt.

With most day-to-day issues companies face, it’s often simpler than it sounds to become expert enough to begin solving real problems. Experience helps, but many challenges simply take dedicated energy and focus. Here are a few repeatable steps you can follow to start down the path:

It often doesn’t take that many loops to become the local expert. While there may be plenty of people in the world that know more than you when it comes to, for example, processes for quarterly planning, you can quickly become an expert in one aspect of quarterly planning processes for your company. If you can distill the experience of the 5 most knowledgeable people at your company into a specific solution, you are likely now more knowledgeable than they are individually in solving this specific problem, which makes your contribution valuable.

Let’s dig into the steps in a bit more detail:

Upfront Work

1) Identify and define a problem

This is a skill by itself, but a good place to start is understanding your company or team goals and looking for what’s in the way. You could also look for opportunities to make changes that would achieve those goals. I like to ask myself prompting questions like: what would it take to triple our output here? Or, what’s going to break when we hire 10 more people into this area? 

Sometimes other people are your best aid in identifying problems — try asking them what keeps them up at night or what prevents them from being as productive as they’d like.

2) Do some basic research

Don’t overcomplicate this — this step is doable in a few hours to a few days. 

Bill Gates suggests asking two questions when trying to solve big problems: “Who has dealt with this problem well?” and,  “What can we learn from them?” Nearly always, a problem very similar to one you’re facing has been solved before. Try searching for things others have written or people in your network or in your company with related knowledge. For this first research section, you’re just trying to learn enough to put together a competent draft. You don’t need to know everything yet, but you want to have enough that you don’t waste other’s time when you start asking for feedback. Save the most knowledgeable or hardest to reach people for The Loop.

3) Come up with a draft of the solution

The goal of the draft is to both 1) to double-check that you understand the problem well enough to generate a solution (if not, you probably need more research), and 2) to give the people you talk to in The Loop something concrete to react to. It’s way too easy to think you’re understanding each other when verbally communicating information. A written proposal, diagram, or presentation forces necessary clarity, which is what you want. Vague feedback isn’t helpful, and if you get vague feedback, either the person you’re talking to doesn’t know enough to comment, or (more likely) they don’t understand what you’re asking. Remember, if you’re taking on a new problem, you have likely spent far more time thinking about this specific challenge than they have. Your draft needs to bring them along on your thinking so far, but also do it in a way that is respectful of the time and expertise they are gifting you.

At this point, your draft doesn’t need to be perfect, as that’s what The Loop is for. It should come across as a faithful attempt to do your upfront work. Once you have that, you can move into your iterations.

The Loop

1) Find someone who knows about the problem

Start with the easiest people to access, ideally someone who has a vested interest in helping you. Maybe your manager or a friend at work. It’s ok if they don’t know much more than you, remember that your plan is still likely fairly weak, and that’s ok right now. Imagine that you are only attempting to bring your idea from 40% good to 60% good in this first pass. Save the hard-to-reach experts for later, when your solution is 95% and you need help getting to 98%. Saving the hard-to-reach people for a final pass avoids looking foolish with a half-baked proposal and also maximizes their value by asking for knowledge only they can provide. By the time you’re getting to these people, you will know a lot more than when you started, and likely your plan will have matured significantly. (Sometimes this can backfire if they tell you something that forces you to start over completely, but you’ll have to weigh this risk yourself.)

Finding the right people to meet with can still be a challenge. Consider asking the people you meet with who they think the best people to meet next might be. You may want to ask them if they’d feel comfortable making an introduction. If they’re not, that’s a great opportunity to ask for feedback about what you could do that would make them feel better about recommending others speak with you (but please don’t push people to make introductions they’re not comfortable with). It could be that the problem isn’t interesting enough or that your understanding or solution isn’t yet mature enough. Hopefully, you have a good enough relationship with this person to get an honest answer.

2) Ask for their feedback, emphasizing critical feedback

In these meetings, it’s helpful to begin by aligning on the problem you’re trying to solve, then tell them you want to run your proposal draft by them and that you’d love their critical feedback. Then, jump into your proposed solution.

Depending on how comfortable the person is with giving critical feedback, you may have to remind them several times how valuable it is for you to hear their critical feedback. You can’t improve your plan and iterate if people aren’t willing to challenge your thinking.

As you’re discussing your proposal, make sure you’re:

  • Checking to make sure they’re following (make a note if they get lost, you likely need to change that part of your presentation).
  • Asking what they think (then really listening to what they say).

Feel free to defend your thinking a bit if they challenge it and you disagree. They may not understand or know the context that went into everything you’re presenting. If you can’t win them over with light defense though, flip from defending into being curious: why are they opposed, how can you make this part better? Even the initial confusion or pushback from them is valuable feedback — something in your proposal lost them. Maybe you need more context upfront, maybe they assumed something different based on other real-world experiences. Whatever the reason, take note of it.

Walking away from your conversation with this person, you ideally should have a solid idea of what resonated, what didn’t, and possibly alternative suggestions for how to improve your solution.

It’s also important to pay attention to how valuable they think solving this problem is. Creating the best solution to solve a problem people don’t think is worth solving isn’t likely worth your time. You may need to scrap this direction and find another problem if you’re not hearing excitement for solving your problem. If that happens, cut your losses and be satisfied that you’ve learned something valuable!

As you wrap up each of these meetings, don’t forget to thank them for their time and their help! Even the harshest critiques are a path to making your solution better.

3) Iterate on your design

After each person you speak with, take some time to use what you learned from talking with them to make your proposal better. This might look like small tweaks to your language in pitching your solution or it could mean throwing away your idea and running with a new idea they gave you. It could even mean deciding to pursue a different problem entirely and starting this process anew.

One of the hardest parts here is deciding what feedback to keep and what to reject. Not everything people suggest will be right. Everyone you talk to will have their own perspective, which will have its own biases or blindspots. As you talk to more and more people, you’ll be better able to identify when that’s happening. Hopefully, as you speak with them, you can share your observations and what you’ve learned to bring them around to a different perspective. If not, that’s valuable data as well. 

If you’re really uncertain if a piece of feedback is helpful or not, make a note to ask the next person what they think.


No solution is perfect, so knowing when to break out of the loop and execute is important. There’s not a clear answer here, so instead reflect on the value of getting it right vs. getting it done quickly. 

The more people you consult with and research you do, the more likely you are to come up with a good solution. This all delays implementation though, and for many complicated projects, it’s difficult to really know if your solution will work until you start implementing it. Consider some of these questions:

  • What are the consequences if I have a false-start on this?
  • Can I learn more as I go?
  • Do I have enough knowledge and organizational support to have a reasonable chance of success? (Reasonable here is contextual)
  • Is this decision a one-way or a two-way door? Relatedly, if I fail the first time, will I get a second chance?

If you’re not sure about the answers to some of these questions, you can leverage your first few conversations to help answer them.

Keep in mind, while this sounds somewhat complex, If speed is important and failure is tolerable, a very lightweight way of running through these steps might look like: spend a few hours researching online, prepare a one-pager with bullet points of your proposal, send it by your boss and 2 coworkers in a google doc and ask for comments. Wait a bit for them to look at it (or schedule some time with each of them if you really need to move fast). Address their comments/feedback. Assuming you don’t get any major concerns and you trust these people to tell you if they had any, you’re ready to go.

As you spend more time in a given knowledge area, you’ll be able to skip the early stages and put together solid proposals the first time. This saves you time and iterations. At this point, you can often just run it by a few people, do some quick iterations, then  move forward. Advancing to this level of problem-solving takes time and experience, but it is a worthwhile goal to strive for. (Don’t get overconfident though, even the most experienced people still look to others for feedback.)

Final Nuance

Following the above steps is enough to solve numerous types of challenges across many types of organizations. It’s simple and versatile, and I’ve had success for both technical architecture challenges as well as things like writing a leveling guide.

If you’re not sold yet, consider also that this process has some side-benefits for you personally as well as for the organization.

  1. As you are discussing the solution with people, you are laying the groundwork for gentler organizational change. In asking for feedback, you’re allowing people to feel heard and in doing so, to feel more bought into your solution. It’s also a chance for you to adapt your solution into one which better works for them, both improving your solution and likely winning their support.
  2. When people hear you’re working on a problem they are interested in seeing solved, some may reach out to offer perspective or help, which then becomes a positive feedback loop. You now have better resources to hone your solution, which in turn will likely lead to more people being interested in helping.

Beyond these benefits, if you are someone who enjoys learning and solving problems, these process guidelines can lead into areas of fun and rewarding growth by providing a way to dive into an area you may not know well, while still granting a path towards solving real problems and bettering yourself and the community around you.

Thanks to Rachael Stedman and Sharon Delaney for the editing help!

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