How to use your network to Pivot

A while back, Phoebe (whose name is not Phoebe) asked Joey (not Joey) for help.

Phoebe had been in operations roles for years and was feeling stuck. She wanted to pivot into a more strategic position at a mission-driven company — but wasn’t sure how to position herself or where to start. “Joey, help! I want to change careers. Do you know anyone hiring for roles like… whatever this is?” she said, waving at a half-baked job description she’d written in frustration.

A few days later, Joey got back to her: “I talked to a couple folks I know in impact-driven orgs. With your background, it’s going to be really tough to land a strategy role without more direct experience or an MBA.”

Did Joey help Phoebe? Technically yes — he brought back feedback. But was it helpful? Not really. Her question wasn’t fully formed, and the answer she got made the problem feel even harder. Joey stopped at “probably not possible,” and Phoebe was still stuck.

This scenario — one person trying to help, the other unclear on what they’re asking for — is painfully common during a career pivot. You're overwhelmed, so you reach for someone you trust. They want to be helpful, but don't know what you really need. And suddenly, you’re walking away with less momentum than before.

That’s the danger of using your network without a clear sense of who to ask, for what, and why.

Who To Ask…

We can all benefit from a little help from our friends. The people in your network can offer camaraderie, experience, pushback, support, and more. Spending time with people in your network when you don’t need help builds trust and understanding. As bonds build, our brains start to earmark things like, “Brent knows how to smoke meat well” for callback in a relevant situation.

We sort people by kindness or by commercial success or by perceived intelligence or by geography or by any number of other traits, characteristics, interests, or skills. And, as individuals, we’re difficult to sort definitively – or permanently – but our brains are hard-wired to try.  So, when you have a need, why do you call who you call?

Many of us seem to rely heavily on one of two filters: 1. Trust and familiarity or 2. Perceived expertise. Under the first filter, when confronted by a challenge, we turn to the people who know us best and who we believe have our best interests at heart. Under the latter filter, we seek out someone’s involvement because we believe they have more or better expertise. 

Both are valid. But both have blind spots.

Your old boss may care deeply about your future but may not understand the space you’re moving into. Your cousin might work in your target industry but have no clue how to talk through a meaningful career pivot. And when you’re entering unfamiliar territory, it’s hard to know who’s actually an expert versus who just sounds confident.

Who To Ask For What…

Before initiating any conversations, it’s helpful to define what you’re trying to accomplish, and incorporate that into your decision on who to call and in what sequence – as well as how and what to ask. 

The trouble is that most of us fall short on distinguishing what we’re seeking, let alone articulating it, and accept everything that is offered. In an effort to be helpful, people often offer up a combo platter seasoned with assumptions and shortcuts that may or may not best serve the situation.

So before you fire off that LinkedIn message or text your old colleague, ask yourself: Would you be best served by clarity (more info, additional intros, hard-won lessons, etc.) or creativity (thought-provoking questions, new ideas, etc.)?

If you need clarity, your ask might be:

• Information: “What does someone in this role typically get paid?”

• Feedback: “How does my resume stack up for that kind of pivot?”

• Introductions: “Do you know anyone who’s worked in a COO role at a startup?”

• Advice: “What would you do first if you were me?”

• Lessons: “What did you wish you knew before you jumped into a new industry?”

If you need creativity, your ask might be:

• Questions: “What assumptions might I be making about this role?”

• Ideas: “What kinds of jobs do you think I’d be good at that I’m not seeing?”

• Wisdom: “What tends to trip people up when they shift from corporate to small business?”

Be intentional. Most people are only great at one or two types of help. Even your smartest, most well-connected friend isn’t likely to offer deep insight and dream up innovative strategies and connect you to the perfect person in the same conversation. 

Who To Ask For What And Why

To frame up a conversation to be optimally helpful, ask yourself two “whys”:

1. Why this person?

2. Why are you asking? 

These questions help you see how you’re sorting the people in your network and what you’re prioritizing when you’re looking for help. In essence, they help you determine why you are asking for ideas from someone or advice from another. Asking for information from a non-expert is a poor decision, as is requesting new ideas from a rule follower. 

So, let’s assume Phoebe chose Joey for a good reason, even if she didn’t get the career advice or help she was looking for. What went wrong?

Let’s start with Phoebe. She was experiencing the stress-induced distortion most of us have when we’re in the flames of a fire and defaulted to “HELP ME!” rather than thinking critically about what would actually be helpful.

And, Joey had options on how he might respond. By asking for everything all at once from the people in his network he deemed relevant, the result wasn’t helpful to Phoebe. He talked to people about what Phoebe said she wanted. There was no thoughtfulness around what information to gather, what Phoebe might actually be asking for, or how those factors interact to frame up a solution to her career challenges.

If he offered questions, he may have helped Phoebe better sort out what she was after and the resulting interaction between skills, opportunities, desired challenges, and options. But she may also have been too stressed to productively engage, in which case Joey may opt to run out the ask. 

Running out the ask depends on prioritizing what you are seeking and from whom – whether you’re the primary person seeking help from your network or someone trying to help in a meaningful way. In certain situations, pure introductions may be the best route. In other cases, the right path might be to run through the steps of gathering information, creating a resume, getting feedback on said resume and then circulating the resume asking advice on where to apply and to what types of roles. Then again, socializing the root problem with someone who may be in a position to offer ideas or wisdom on alternative solutions and sharing the resulting ideas with Phoebe may yield the most productive path forward. 

Making the ask land

When in doubt, zoom in or zoom out:

• Zoom in for clarity: “Can you help me pressure test this cover letter?”

• Zoom out for creativity: “What kinds of roles do you see me thriving in?”

Then refine your ask based on what’s working. If someone gives you a useful next step, great. If not, regroup and try someone else with a better fit. Don’t ask for everything all at once. Don’t assume the first dead end is the final word. And don’t confuse familiarity with usefulness.

Most people want to be helpful. So help them be helpful. Figure out whether you need to zoom in (clarity) or out (creativity). Source and phrase your requests accordingly. Then keep refocusing until you have what you need to keep going, keep exploring, and keep pivoting.