Site Overlay

Would you mind sharing job seeking advice?

This is a common question I get asked by both seasoned experts and students interested in software product roles. I love helping people explore their paths and find that the best advice is to share how I’ve gotten to where I am in order to help them.

Below is the framework I provide for high achievers in mid to senior level roles. I’ve deleted specifics to respect anonymity

It’s time to look for a new job. I’m struggling with how to decide when to reach out, to whom, to how many. 

– anonymous

When to reach out, typically depends on how fast you need to find a role. It usually takes 6-8 weeks to find an industry standard role if you are organised, prepared and remain local in major cities like Seattle, Berlin, San Francisco, New York City and so on. 12-18 weeks if you reach out to your network, apply to roles daily and look outside of a major city. 6-12 months if you are casually searching and have specific requirements. Keep in mind, the more focused and specific your role expectations can add additional time from my estimates.

What to expect:
Connect with your network and reach out to recruiters. Start with people you have worked with before who know the value you provide. Ask them to introduce you to at least 2-3 people in their network. You can use this time to connect and understand what other people are excited about in their roles. Now would be a good time to practice sharing what you are excited about and what you are looking for. (Use and refine your manifesto)

Email, LinkedIn, text messaging and using Google docs are going to be the best tools for reaching out to your network and tracking conversations.

When the time comes, use LinkedIn jobs and Indeed to apply for roles. These have netted great results for me.

Initial conversations are often voice or video calls. Be sure to set up common apps such as, WebEx, Skype, Google Meet or Hangout, and Zoom installed.

Tip: Check out this link on how to better prepare for video calls.

Initial calls start with a recruiter and the second is the hiring manager. If conversations go well, next steps can be a peer interview via a call or directly to an all day on-site interview.

Tip: When speaking with a recruiter have your latest CV or Linkedin profile at the ready. This will help you read through it with the recruiter and you can both follow along in the same order. Plus, it can help prompt you in speaking about achievements you might otherwise have forgotten in an interview situation.

Tip: You will learn a lot about yourself and what you want by just going through this process. It doesn’t mean you need to take a job! You can gain confidence in your current role as well.

Prepare: Schedule as many conversations that you are comfortable with on a weekday or in a week. These can be exhausting and require lots of talking. I would suggest no more than one a day.

Another Tip: Set up a doodle meet me request or calendly. These are examples of apps that connect with your calendar service and provide scheduling requests for your network and recruiters so you can quickly schedule time.

Here is the approach I took February through April 2018:

I was aggressive. I filled my days with interviews and networking chats. At least three times a week for three solid weeks. All my progress chats, email exchanges and thoughts were tracked in Google docs. I also took prolific notes on each conversation to reflect upon later.

Ask yourself these questions in order to start targeting your next role:

  1. What skills do you have? Do you want to continue doing the same thing?
  2. What are the skills you want to learn next?
  3. What product area or type of project do you want to do? Service, hardware, Platform and so on?
  4. How long has the company been around for? 1 year, 3 years, 5 years or 10 years, or 25 + years.
  5. Is there a company type that you get excited about? Consultancy? Startup? Corporate? Early phase? Late phase? Hyper growth?
  6. What company size would you consider? 10, 50, 100, 500, 5000, 50,000 100,000+.
  7. What type of cultural values are you looking for? Are they similar to your values?
  8. Is it important for you to know people at the job? or team connection?
  9. Is your manager important and do you need a connection?
  10. Commute? Are you open to locations in Seattle? Redmond, Bellevue?
  11. Does your level matter to you? Manager? Lead, Head of? Director? Etc?
  12. How much does $$$ matter?

My ideal situation is that I have reviewed current official openings and found a couple of roles that excited me.

– anonymous

This person already had an idea of what they were looking for. Start applying and reach out to your network that knows people there. Browse your LinkedIn connections and identify 1st or 2nd connections. Reach out directly to those you know and ask them what they think and if they are willing to chat about how they are doing. Another approach for 2nd connections is to ask to be introduced to their contact or connect directly with that person if their profile allows for it.

 I would also like to reach out to awesome people I want to work with again, to see If they have something coming up that I may not have seen officially. 

– anonymous

Do it! Make a list and track it. Use my personal template. I tracked every conversation when I reached out. What I did last informed my next steps.

Then I’d apply, and try to line up multiple interviews so I can compare my impressions and choose what fits best.

– anonymous

Yes! I did a list. Here are my top roles with scores applied to each of my values. Similar to a priority matrix.

But how do you do this and keep everyone feeling like I want their job the most? 

– anonymous

When I’m interested in a role I am genuine and authentic. However, If you aren’t feeling it at any point, it’s ok to decide to say thank you, but not right now. I asked questions around my areas of doubt. If you have concerns in a certain area, ask questions around that topic. Sometimes I knew something sounded off or undesirable. See more thoughts on this below. I would question my doubt too. I never quit before I felt I had the big picture. Wrap up and keep open communication and don’t drop the ball on email communication. 

How do I reject a contact’s offer without sounding like I think their work is boring? 

– anonymous

Dig in deeper, ask your contact questions around this topic. If it sounds boring, try to find out why. How can you understand why it’s boring? What questions could you ask? This might help you and they could help you see your perspective opportunity differently. I found every candidate who asked me questions made my case stronger as an employer. Think about how you have rejected candidates as peers. It’s the same. You are interviewing an employer as much as the employer is interviewing you. FIT IS IMPORTANT!

I think I have a good chance to land an interesting job, but I don’t want to be arrogant about it…


You have a GREAT CHANCE. You are smart, you take feedback well, and you’re experienced. You are amazing to work with and I believe you will have no problems. I don’t beleive you will be arrogant. The fact that you are saying this means I doubt you will be. If you feel arrogant, find out why. This might explain fit. I find it’s not the effort but the dynamics of the team manager or other factors that don’t feel right. 

Example: I was chatting with a friend on my old team, and he said I should come back. They would surely find a position for me. But I’m not ready to explore it, as I’ve already been there done that. But it is a good team, and I know I did well, so I’m open to it. It makes sense, just don’t make it look like it’s a fall back.


I’d still find out more. It’s a conversation. This is networking and informational as much as it a job interview. Ask the right questions and practice talking about you!! Your goals. I find that it helped me understand what I was looking for. I modified my goals with every conversation. It became clearer what I needed and wanted.

Then I was chatting with peers and their partner was asking advice about remote jobs. I happened to ask this person if they had anything. They found a UX/Innovation focused position on an incubator team. But I’m not sure I would want to work on technology that I’m not actually using myself. At least not as my first choice. But I can’t really say that, right?


Sounds fine. Find out more. I’m finding more people working remotely as time goes on, it’s becoming the norm. I’ll be joining Shopify and you should feel free to ask those questions. Ask people in the current team if they have used the technology before. How did they get passionate about it? What are they most excited about? Maybe something they say will sound interesting and it will just click.

Wrap Up

It’s okay to reject early on. I was in the phase of learning so I said “yes” to it all. I It’s okay to be rejected and to reject others early on. I was in a learning phase so I said “yes” to it all. I continued to open a large funnel. I reached out to everyone I thought of and applied to many places. Emails, LinkedIn intros and more. I would sometimes get three intros. Then those turned into three more. I did this because I had to. Time was a constraint for me because of my visa in Germany and of course, money.

It was insane. The challenge is knowing your limits. So if you can’t do more than 5-10 calls a week, then don’t push yourself!!! I was under pressure and I took on more than I should. This meant my energy levels were super low. Some I declined early. Some were mutual declines. At times, I was declined and was bummed. I learned tons about my family and myself. For instance:

  1. I want to be a PM because I want to learn (design role challenge didn’t excite me during the on-sites) 
  2. My family doesn’t want to live in Berlin 
  3. Culture is super important, but the hiring manager and leadership team is even more important
  4. I didn’t want to be an executive for a while until my kids are much older
  5. I want to test a space that’s not a social product (first time ever not in my domain) This means many more learnings.

Thanks for reading this. Also if you found this useful let me know!
p r a r @ u n l i k l e y p a t h . c o m .

Good luck on your next journey!

Leave a Reply

Copyright © 2024 Unlikely Path. All Rights Reserved. Thoughts | SimClick by Catch Themes