Posted on by Nick Korte

Own Your Job Search: Be the Captain, Find a Harbor Pilot

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Cruise ship captains rely on the expertise of a local harbor pilot to safely dock the ship at a port. What if we as the captains of our careers sought the expertise of a harbor pilot to help us navigate a potential employer and their processes? Not sure how to find one?

This week in episode 317 we explore this analogy of the captain, the harbor pilot, and how the collaboration between them makes for a safe docking event. We’ll talk through what a harbor pilot might look like, how you can be a harbor pilot for others, and how you can find one for yourself.

Original Recording Date: 02-20-2025

Topics – A Topic Idea from Taking a Cruise, Common Mistakes of the Captain, Understanding the Harbor Pilot, Finding a Harbor Pilot, Wrapping Up

1:01 – A Topic Idea from Taking a Cruise

  • Today’s episode is just John and Nick. We’re taking a break this week from having guests and want to share a topic based on a personal experience Nick had recently.
  • Nick and his wife like to take cruises, and on a recent cruise he attended a special panel discussion with the captain and other senior officers. After some discussion about the jobs and careers of the captain and his senior officers, someone asked a very interesting question, and the answer to it gave Nick the idea for this topic. Here’s the question:
    • What is the role of the harbor pilot that boards the cruise ship before we dock in every point?
    • The collaboration between the captain of the ship and the harbor pilot is what allows safe docking of the ship at a port. This concept gave Nick an idea of how this can apply to searching for jobs.
    • The captain in this analogy is the job seeker. The harbor pilot is a person with expert knowledge of a company who can guide you (someone who knows where you’re headed).
    • What is the split in responsibility of the captain and the harbor pilot?
      • The captain knows everything about the ship / vessel and is in charge of all operations. They know the capabilities of the ship. The captain knows the ship’s planned course of sailing and the approach planned for docking at a specific port. There is an entire bridge team working to operate the ship, and all are accountable to the captain.
      • The harbor pilot has expert knowledge of the port. They know the weather patterns. They have worked with many different ships and are there to help the captain dock the ship at a specific port.
      • Regardless of what the harbor pilot says or brings to the equation, the captain makes the final decision on what will be done. Even though their collaboration is a partnership, the captain has to be the one to give the orders. A captain has to take in the guidance from the harbor pilot through the lens of what the ship can do. The captain may choose to follow the harbor pilot’s advice or go against it in some cases.
    • John sees many implications here:
      • Am emphasis on collaboration between the 2 roles
      • The captain has ultimate responsibility for the outcome of the ship regardless of who they collaborate with. The captain has to own the decisions.
      • “You’re the captain. You’re ultimately responsible…just like if we are job seekers or managing our own careers, we are ultimately responsible for the outcome of that career.” – John White

4:55 – Common Mistakes of the Captain

  • What are some common mistakes that a captain (or job seeker) might make?
    • John thinks of not taking responsibility or just handing over responsibility for docking the boat to the harbor pilot (i.e. becoming a passenger and just doing what you’re told rather than being the captain). What does that look like in greater detail in a job seeker?
      • Nick says maybe it is going wherever the wind blows you or only considering opportunities that come to you.
      • This could also mean you didn’t do any planning. The captain has to chart the course for the entire voyage including the selection of routes to take and the order in which the ship will visit ports.
      • Have you researched the company to learn as much about the culture as possible?
      • Are you prepared to answer technical or other kinds of questions?
      • Have you thought about the questions you want to ask in an interview, and do you know how to ask questions that suit the way you like to work as discussed in Episode 314 – Make Goals Inevitable with ADHD: Stressors and Entrepreneurship with Skye Waterson (2/2)?
      • “Here’s the part of the sea that I’m in. These are the potential ports, and I need to know if my ship is appropriate for that port. That’s some of the deep research, And then, once we decide as captains of our careers that we actually want to do some much, much deeper investigation of a specific port, of a specific career branch or an organization to go to…we need to actually navigate how to dock….” – John White
      • Other examples would be blindly applying to a company without doing any research or relying too much on a recruiter to help you navigate the opportunity (i.e. being too passive and not following up when a recruiter doesn’t respond in a timely manner).
    • At some point, the captain has to make a decision whether to take advice as it’s given by the harbor pilot or to adjust it / go against it because the captain knows the ship better than anyone just as you know yourself better than anyone.
      • Maybe a harbor pilot is used to more container ships, and a lot of the advice you get is geared more toward other types of ships. You as the captain have to know your unique capabilities and take customized action based on the advice.
      • Listen to Nick’s example of this scenario from a recent cruise. The captain knew the ship had a particular type of propeller that could be rotated to hold the ship close enough to the dock / pier so passengers could safely enter / exit after someone had parked a small boat in the path of the cruise ship.
      • “As the captain…the outcome that you need is not just docking, but you need…a way to get your passengers on and off…. It’s not just landing at the company. It’s landing with the right role with the right team.” – John White
      • Nick says an obstacle in your way at the pier may require a different approach like we discussed to dock safely, but in a different scenario it could also be a red flag indicating you (the job seeker) don’t visit the port at all. John gives the example of very non-standard job roles being a red flag at a company.
    • The other end of the spectrum would be ignoring all the advice about the port (a company) or not seeking advice in the first place. This assumes you are the expert but have also ignored local knowledge and local context.
      • How many times has the captain even visited that port compared to their overall time on the ship? Nick argues that we can’t be experts at the port where we’re trying to dock the ship. The harbor pilot helps ships dock at this port on a daily basis.
      • John feels like he has made this mistake before. About once per half, if a recruiter reaches out, he has a conversation with them to understand a specific role and practice interviewing skills. John stresses the importance of our need to maintain interviewing skills. At times John has approached these conversations without the same level of preparation as when he is seriously interviewing (i.e. not even looking for a harbor pilot).
      • Nick has made a similar mistake. Sometimes recruiters have reached out with an interesting role, and he was just too busy to dig deeper other than saying thank you. That’s kind of like disregarding the port as a possibility.

13:35 – Understanding the Harbor Pilot

  • We said the harbor pilot has expertise on the port itself. What might the harbor pilot look like at any given company?
    • This could be anyone who currently works at a company or who has worked there in the past. This person would understand how the company runs internally and details of what a role is truly like.
    • Nick says connecting with a harbor pilot can help us set the right expectations when considering a job at a specific company. It sets expectations about docking the ship at this specific port and how you might do it safely.
    • John says the person acting as a harbor pilot may understand internal priorities and how to navigate those. It could even be someone who has gone through the interview process at the specific company for a similar role, even if they don’t work for the company currently. People who have gone through the interview process at this company in the last 6-12 months will be more helpful than those who went through it 5 years ago, for example.
    • John thinks the harbor pilot could be people at the company who interact with the specific role you’re targeting.
      • If you’re looking for a role in sales engineering, maybe you seek out someone in professional services or technical account management.
      • If you’re looking for a role as a cloud engineer, consider people in IT Operations, architecture, networking, or perhaps even cybersecurity.
    • If the company provides goods and services, what about finding someone who is a customer of that organization?
      • Ask the customer how their interactions have been with that company just in general.
      • If the customer works with representatives of a company on a regular basis (i.e. like working with representatives of a technology reseller), it provides insight into the responsibilities of different roles at the company.
      • Customers who are part of a formal advocacy group for a vendor’s technology solution may have even greater context to share on the roles and responsibilities of people at that vendor and the overall company culture of the vendor. Advocacy program members may also have good relationships with employees at the vendor and could be willing to connect you with someone to have a deeper discussion.
      • Loving the technology being used at a company (regardless of the role you are seeking) is one sign it might be a nice place to dock your boat (but not the only sign, of course).
    • Nick thinks we would turn to our immediate professional network first. Hopefully we have kept professional connections warm over time. Ramzi Marjaba had some great suggestions in Episode 307 – Sales Skills: Professional Networking and Continued Practice with Ramzi Marjaba (1/2) even if you haven’t.
      • If you reach out to someone, be honest about what you’re trying to do and the help you need. All they can say is no.
    • John realizes he has acted as a harbor pilot to others who have reached out to him in the past. Nick re-iterates that John was his harbor pilot for a particular job in the past.
      • Several years ago, when John was a harbor pilot for Nick…he referred him, explained the process, shared some of the expectations of the role, etc. But, in this case, Nick was still the captain.
      • More recently, when people have reached out to John, he has offered to have a conversation with them. John will provide context to the person on the organization, even if the open role is in a different group from where John works.
      • A harbor pilot might be able to give insight into the skills required for a specific role and how it has changed over time as a result of the company’s direction. Nick refers to this as some of the stuff that might not be in the job description.
      • John says the words on a job description may mean a very specific thing within the context of a specific organization. When he was at Google, one of the interviews was to determine how “Googly” a person is. It meant something very specific.
      • To take another example…if a company says it is looking for people who can embrace change, what does that mean for that organization? Does it mean job responsibilities might shift every 6 months, you have a different manager each year, that you might have to relocate, etc.? You need a harbor pilot to tell you.
      • The harbor pilot has more context on where you’re going.
    • Nick thinks a great recruiter could be your harbor pilot. He remembers in times past working with excellent recruiters who helped and guided him through every stage of the interview process.
    • Nick says some of it is going to be determined with how much rapport you have built with the person you want to be your harbor pilot. With good rapport established, people may be willing to introduce you to others they know perhaps without you needing to ask them to introduce you.
    • John gives the example of having systems engineer in your title. Sometimes you might be contacted by a recruiter for a role with the same name but in an industry that uses the term differently.
      • In manufacturing, for example, a systems engineer may be responsible for integrating the hardware manufactured with the software.
      • John will usually take the time to politely explain to a recruiter what his experience has been as a systems engineer (in this case working inside a sales organization) so the person understands the nuance in the role across different industries. Even this exercise builds rapport and could lead to future opportunities down the road from the same recruiter.
      • Recruiters in California are not allowed to ask candidates about their current salary. In addition to sharing that he is not interested in a role or that its pay range would not be enough to want to change jobs, John can make the recruiter’s life easier by sharing his salary requirements.
      • “The more vested a recruiter is in landing you, the better…harbor pilot they are going to be…. When they feel like now they’re a little bit more invested in you, that’s when they’ll be way more communicative.” – John White
      • John has also had recruiters give him additional context about why they reached out to him over others (i.e. a need for specific skills / experience, etc.) which might step beyond what the job description says. The key recommendations from John on this are building rapport, being open and transparent, and continuing with a conversation.
    • Nick reiterates that we shouldn’t discount our own ability to be the harbor pilot for someone else.
      • “Wherever you work, whatever you do, whomever you know…you could be this for someone else seeking a job. And perhaps, if you have done that for somebody else and they get the job or they have a good experience…you’ll understand the flip side of that coin.” – Nick Korte, on being the harbor pilot for someone else
      • John says we might reflect more on it if someone for whom we have been the harbor pilot gives us feedback on their experience and the value we provided along the way.

26:31 – Finding a Harbor Pilot

  • There are many people who could be a harbor pilot for you, but how do you find them, engage them, and get them to help you?
    • The harbor pilot has a vested interest in your success. Crashing the ship can also be a poor reflection on them.
    • We mentioned it earlier, but immediate LinkedIn connections are one option.
    • Try looking through job descriptions for the top technologies listed as required competencies.
      • Look for community groups centered on these technologies (on LinkedIn or otherwise) in your area (or even outside your area). Finding and connecting with these community group leaders might be helpful to gain insight as to what types of companies use specific technologies. Community group leaders may even know someone at the company that has the job opening or help you make a connection that could help in some way.
      • John doesn’t recall looking for a Nutanix User Group or even a virtualization user group when he was interviewing for his role at Nutanix. He could have tapped the community to get their point of view on Nutanix as technology vendor, etc.
    • If you’re in a role at any company and deal with vendors or technology resellers, try asking them if they have worked with a specific company to get a perspective. Don’t do this using your work e-mail account, of course!
      • Resellers of a specific technology can speak to interactions they have had with employees of different vendors.
      • Perhaps the vendor you work with could introduce you to someone they know at a specific company who could help (i.e. someone who would be willing to do an informational interview). We discussed informational interviews with Mike Wood in Episode 169 – A Thoughtful Personal Sabbatical with Mike Wood (2/2).
      • John has both given and asked for informational interviews in the past. The purpose of them is to gain more information on the company and not an expectation of it being a formal interview with the hiring manager. John tells the story of having a good conversation with a friend of a friend at Nutanix before he joined that was extremely helpful.
    • Try to think through who to reach out to through the lens of what is most important to you in a job / employer.
      • Is it company culture, being paid well, great benefits, what managers are like, etc.? Your priorities might help you choose who you know that could speak to these points. GO back to the Must Have List created by the hosts of Real Job Talk.
      • If you are actively managing your network and genuinely listening to people over time, you will understand what different people in your network care about. If they care about the area you want to know more about, ask them if they know anything about the specific company where you’re interviewing (or even its competitors) that can help you.
    • John finds the analogy exciting and is starting to view some things we have discussed in the past through a different lens.
      • We’ve been discussing actively managing your network, reaching out to people, and the importance of getting people to help us navigate situations and organizations.
    • We spoke about being a harbor pilot for someone else. What if we reverse engineer that situation where we are a harbor pilot to someone else?
      • Think about the connection the person who reached out had to you. Understanding the connection might help you identify ways to find your own harbor pilot through similar connections. Maybe that’s another outside the box way to help yourself find a harbor pilot.
      • Be curious as to how people found you and why they reached out if you’re giving an informational interview.
      • You might have a blog, a podcast, or something in your LinkedIn or social media profile that makes you more approachable because your work is in the public eye. This applies to others you could reach out to for help.
      • Asking some questions of the people who reach out to you for help will make you a better interviewer and sharpen questioning skills for when you are in a job interview situation. By asking you for help, the person asking is interviewing you. Taking the time to have a conversation allows both them and you to practice interviewing.
      • One of the best books Nick has read in the last year is called Talk to Me by Dean Nelson. Nelson is a journalist who wrote this book about asking better questions and being a better interviewer. Nelson breaks down popular interviews and the questions asked, and it is fascinating. The concepts discussed in this book apply broadly across many fields. Reading this and internalizing the lessons will make you a better job candidate and a better job interviewer.

36:30 – Wrapping Up

  • You are the captain. You make the final call, and you have to own the decisions. You should know everything about your ship (as much as can be known) and have a willingness to take advice from the harbor pilot.
  • Seek expert guidance from a harbor pilot, and have a true collaboration with them. Accept that they are experts at something you can’t be an expert at (your ship at their harbor).
  • We discussed what the harbor pilot might look like and how to find them. Maybe acting as a harbor pilot for others will help you find a harbor pilot in the future.
  • In the maritime world, the harbor pilot has to come help the captain of the cruise ship. It’s mandated by law.
    • In the case of the job seeker, it is going to take some work to get the harbor pilot onboard. It likely will not be given to you. The responsibility and planning have to be there if you truly want a harbor pilot to help you dock.

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