Why does something I know how to do suddenly feel difficult?
You get into a new job, recognize a familiar problem, and think, okay, I know how to handle this! You have done it before after all. You have a process, a framework, or a way of organizing the work that has been successful elsewhere.
Then you try it, and things don’t move the way you expected. People push back. Decisions stall. You follow the same steps, but you get a very different result.
The system rejects your expertise.
That can be super frustrating, especially when this was something you felt confident doing. It can also be tempting to conclude that the people at this company just don’t understand how the work should be done.
And sometimes, when we get into that mindset, we start becoming defensive which causes the system to reject it even harder.
I know this… because I was that person on more than one occasion. It’s a hurdle that everyone has to overcome in order to progress their career.
But one of the first things I would explore is what made your approach work in the first place. Because some of those conditions may no longer be there.
What did my old approach depend on?
Your process existed inside a particular environment. Maybe everyone involved already understood the problem. Maybe you had direct access to the person who could make the final decision. Maybe the scope was smaller, the timeline was longer, or the team had resources that your current company doesn’t have. Whatever it was, the context (system) that your work was done in matters just as much and maybe even more than the work itself.
Those things can become so familiar that we stop noticing them. We remember the steps we took, but we don’t necessarily remember everything surrounding those steps that allowed them to work.
For a hypothetical example, imagine you used a short weekly meeting to move product launches forward. At your previous company, everyone who could approve the next step attended. They knew the background, discussed the problem, and made a decision.
At your new company, you run that same meeting. But the people attending have to take every decision back to somebody else for approval. A week later, you’re still waiting.
Adding another meeting may do very little, because that’s not really the thing that isn’t working. It’s the fact that decision makers are a game of telephone away.
First, you need to understand who can decide, what information they need, and how a decision actually gets made here. Then you can design a process around that reality.
The meeting was useful because of what it allowed to happen. Recreating the meeting alone doesn’t recreate those conditions.
See? That’s the difference. It’s not about whether a meeting worked before (because that IS what you will focus on) it’s about what did that meeting allow to happen!
Do I understand the method, or have I practiced the steps?
This is one of the reasons I separate knowledge from skill when I talk about developing your craft.
You can become very practiced at doing something a particular way without having explored why that approach works, when it stops working, or how you could accomplish the same thing differently.
Earlier in my product marketing career, I gravitated toward structure, formats, and frameworks. I would bring those approaches with me across companies and teams. As my knowledge developed, many of those frameworks changed or went away. I understood more about what they were trying to accomplish and how that needed to change in a different business.
I learned this the hard way when my frameworks would work brilliantly at one company and fail miserably at the next. And this was a lesson I repeatedly had to learn and readjust to.
A question I like here is: If I couldn’t use my usual approach, would I know another way to accomplish the same purpose?
If that is difficult to answer, you may have found something worth learning more about.
How do I decide what needs to change?
Start with one specific point where your approach stops helping. You don’t need to redesign the entire organization. (I mean, you could try but good luck with that one!)
Write down what that part of the process was meant to accomplish. Then compare what was available in your previous environment with what is available now.
And talk to the people who already work here. Ask how they handle similar decisions, where work tends to get stuck, and what they need from you. They may know something about the environment that you haven’t had a chance to learn yet.
Choose one adjustment connected to the difference you’ve identified. In the meeting example, that could mean arranging the appropriate review before the team commits to a launch decision. You can then observe whether decisions actually move forward.
Some obstacles will require support from your manager or another team. Recognizing that you lack the authority, resources, or agreement to move forward is also useful information. Adapting your approach doesn’t mean taking personal responsibility for fixing every condition around you.
And most importantly focus on these two things that I tell anyone I coach:
- Stop trying to guess! The answer to what people need is already there, just ask them.
- Focus on delivering high impact quickly! Spending months on months on a project means you’re delivering no value along the way.
What does this have to do with developing my craft?
Your craft includes your judgment about how to approach the work. That means understanding when a familiar method helps, what it depends on, and when to change it.
So take one approach that is struggling now and ask yourself: What was I trying to accomplish? What helped this work before? What is different here? What small adjustment could I try, and how would I know whether it helped?
Your previous experience is still useful. Understanding the conditions behind it gives you more ways to use it.
