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Identify & Learn From Tech Connections


April 29, 2022

Job Search Strategy, Pivoting into Tech

(Photo Credit @aaronburden)

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I hope you’ve enjoyed reading this ‘Pivoting into Tech’ series as much as I’ve enjoyed sharing it with you. Over the past few days, we’ve focused on setting goals, making space, and managing your current job. Much of that was focused inward, on prepping yourself and your loved ones for an impending change. Today we will direct our energy outwards and instead focus on how and why it’s important to speak to people who work in the tech industry very early in your search process. 

  1. Start with people you know & trust

    • Try and learn from trusted connections about the new industry you want to move into. While it’s also very important to do your ‘book learning’ to gather info about an industry, you also want to hear about an industry directly from the people working in it. 

    • They can tell you what is overhyped in the media, and what is spot-on. They can share tips on what to highlight in your resume and on how to get in the door at specific companies. These initial connectors are often a treasure trove of information and you should treat them as important resources. And because you know and trust them, the barrier to starting your outreach is much lower (especially for those who are not big fans of networking). 

    • Make sure to stay in touch with these initial helpers throughout your search (as they are the ones most often to be forgotten after one call).  

  2. Identify 3 friends/connections who work in tech

    • The rule of 3 appears in many places (including survivalist training and writing principles). And so I’m applying it here in networking too. 

    • Start with 3 people. That’s all. It’s a nice small number that gives you a varied enough perspective on tech, but isn’t an overwhelming task to speak to ‘everyone you know’ in tech. 

    • Look for people who are in roles and companies you are considering. Try to aim for connections who are at or just above the level you are seeking, as their information will likely be the most relevant. 

  3. Widen your circle of contacts

    • Don’t have those 3 connections, or want to broaden your tech network? Think about how you can leverage your current network to make introductions on your behalf to those who do work in tech. Try to find others who share common interests besides tech as it will help you overcome the cold of an initial outreach. 

    • LinkedIn is an amazing discovery tool to help you find people. Did you know that you can use the filters to search specifically among the connections of one of your connections? It’s incredibly useful to use if you have that one friend who knows everyone (but can’t pluck names out of thin air). 

    • You can also use filters or keyword searches to search for potential connections who share the following: fellow college alumni; past company colleagues; live in your area; share hobbies or interests; have the same country of origin, etc. 

  4. Ask for their guidance

    • When drafting a good tech networking email, it should start with who you are & your connection to the recipient. You should let them know why you reached out to them specifically, not just a generic message you cut/paste to everyone. And it should include a few open time blocks or a scheduling link to help make it as easy as possible for someone to decide to give you time.  

    • Reach out to tell them you’re considering a move into tech and would appreciate their advice on how to get started. Maybe they made the same move you did? Maybe they work in the area you are fascinated with?

    • Schedule informational interviews to learn why they work in tech, what you need to know about company cultures/operating styles, and the skills needed for your target role(s). Make sure to write up questions in advance and order/prioritize the list. We’ll use the information you’ve gathered to help develop your specific tech career search strategy. 

    • At the end of every call, ask if they have 1 person they can connect you with to learn more about tech. And then make sure to follow up with that person!

  5. Keep track of your networking!

    • This is the number one thing that many job seekers underestimate in importance. Tech recruiters are ridiculously busy & overworked these days - and most don’t have time to network. Instead, you want to engage with people in the functional roles you are considering. 

    • Your network is vitally important to your success in getting your resume reviewed! And so it’s also important to keep track of your success with networking outreach. 

    • Check out this post for a great personal CRM tool to use! And then keep track of your networking stats/ratios. You want to know how many cold emails you’ve sent, how many converted to conversations, and in future, how many offered to make referrals. Tracking these stats will help you determine what to tweak in your networking approach as well as mitigate rejection frustration when some don’t respond. 

Learning from people who work in the industry is a really important step that many career changers skip. I often hear job seekers say they don’t want to ask dumb questions, so they opt to go straight for resume editing. If you approach it in the right way, informational interviewing can provide incredibly valuable insights that will help you better target your search and help you grow the relationships that will help you succeed in your new company/role. 


Managing Your Current Job for a Successful Transition + Registration is open


April 29, 2022

Job Search Strategy, Pivoting into Tech

(Photo Credit @aaronburden)

INTERESTED IN JOINING THE DIGITAL ORCHARDS FELLOWSHIP TO HELP JUMPSTART YOUR TECH CAREER PIVOT ALONG WITH A SMALL COHORT OF AMBITIOUS INDIVIDUALS?

JOIN THE WAITLIST HERE: DIGITAL ORCHARDS FELLOWSHIP


As we continue on this ‘Pivoting into Tech’ series, today’s focus is on how to best position yourself for a successful transition. You should be thinking about how you can leverage your current role for the next one - and how to not burn bridges behind you.

  1. Plan to Leave with Grace 

    • Consider how you’d like to handle your current job and what kind of departure you’d like to architect. We all love to hear the stories where someone left a company in a blaze of glory, spilling secrets & bad-mouthing management the way you secretly wish you could. But in reality, doing that that will hinder your progress forward in the new role if anyone hears about it (which they will).  

    • Instead, try to think of someone you admire for how they planned their departure from their role. How did they approach keeping up their work product? Their work relationships? The timing of their announcement? It’s better to emulate someone you admire for their ability to design a good departure that shows it can be done. You’ll leave with no regrets. 

  2. Be Aware of Promo/Bonus Cycles 

    • Not everyone has the patience to think about this but it’s worth the effort in the long-run. I had a colleague who was so excited about moving to a new startup that she almost left 2 weeks before our yearly bonuses came out. I convinced her that two weeks in the grand scheme of things wasn’t worth forgoing a healthy financial bonus that she had earned through her hard work. 

    • Are you close to getting a yearly bonus? Aim to make your transition after that date and use it as motivation. You can still be making moves & applying to other roles - just don’t tell anyone yet. 

    • Are you going to be up for promotion soon? I’d advise you to focus on your current role, get the promotion, and then start to make your pivot. You’ll be able to command a better salary and/or title in a new company by leveraging your recent promotion. 

  3. Move your current job into ‘Maintenance Mode’

    • Maybe you’re not interested in bonuses or promotions - you just want to get out asap. Or you’ve already gotten one or both - and your departure is now imminent. 

    • Think about how to move your current job into ‘maintenance mode’ so there are no complaints about your work, but it frees up your brain to learn new things about tech. This will also give you extra time in your week to be sending out applications and building new relationships to help you make the move. 

    • Some clients feel guilty about this tactic but that’s why I highlight the part about no complaints about your work. If you’re a high achiever, it’s hard to just do your job adequately (vs to the absolute best of your ability!) But if you’re not pursuing a promotion, I give you permission to just be average for the next few weeks. You need that energy redirected to your future move. 

  4. Keep your connections with colleagues

    • While I don’t advocate telling anyone that you are leaving until you’ve secured your new role, that doesn’t mean you can’t be intentional about solidifying your relationships with work colleagues that you value. 

    • Take a minute to identify the colleagues who you would like to maintain relationships with once you’re at your new company. What’s the best way to stay in touch with them? Check out this post for a great personal CRM tool to use!

    • Think about whether you want to send individual goodbye emails to these folks or schedule 1:1 coffee chats when you’re ready to leave to highlight your appreciation for being great colleagues. 

  5. Start building a transition guide

    • For some people, starting a transition doc can help make all of this seem more real. You don’t have to spend a ton of time on this now, but jotting down a few notes will help you start to make your transition a bit smoother for everyone. It can also contribute to your ‘making moves’ mindset. 

    • Start a document where you list out your main project(s). Make sure to highlight dates, collaborators, goals, budgets, and status. You can also keep collecting projects and documents you’re working on in one folder. 

    • Note: this can also be useful if you are going up for a promotion as it helps you see the project(s) where you provide essential contributions because you probably wrote those down first. 

I remember clearly that for two of my job departures, I was commended by my managers for being intentional about how I planned my exit & handed off my work so the organization could keep moving forward. 

You should aim to do the same thing as your network is a source of great value in your career - and you want others to remember you as someone who demonstrates care alongside your ambition. 


Find Extra Time and Space to Focus on Your Career Pivot

(Photo Credit @aaronburden)


Interested in joining the Digital Orchards Fellowship to help jumpstart your tech career pivot along with a small cohort of ambitious individuals?

Join the waitlist here: Digital Orchards Fellowship


Yesterday, we discussed how to take stock of where you are in your career & then how to start envisioning your future. You can view that post here: Take Stock + Envision your Future

For many clients, that’s the fun part: looking towards a bright & successful future. And many job pivoters stay in that phase - and don’t progress forward to make that vision a reality. 

Why? There are a host of reasons that can give someone pause when making a career pivot. It’s not the right time to make a move; you realize it’s not the right industry for you; a family situation delays your move, or an unexpected promotion comes your way and improves your current job situation. All of these are among the many valid reasons to stay where you are. 

Today, I want to explore one common challenge to moving forward that is often overlooked but easily addressed: you, the job seeker, haven’t prepared the groundwork to give yourself the time and space to make this change.

  1. The Reality: Job searching takes time 

    • It happens all the time. A potential client says I’m ready to get a job in tech - can you fix my resume? The assumption is that all you need to do is change some words on a paper & that’s enough. Actually, it takes thoughtful review of your current situation & skills to map out a good plan for making a career change. 

    • You will need to open up extra time & space in your life to make this pivot. How are you going to do that?

  2. Map out the tradeoffs you are willing to make

    • Sit down and estimate how much time you can realistically devote each week to making this career change happen.

    • Then try to identify how much time it will take to make the pivot. You can guesstimate that it’ll take one month for every year you’ve worked - but this depends on how big a pivot you’re making, what your transferable skills are, and the networks you can leverage (we’ll cover these a bit more over the next few days). It’s good to have a realistic set of expectations. 

    • Then write up a list of tradeoffs you’re willing to make with yourself, your spouse/partner/family, volunteer commitments, etc.

      1. Maybe this means skipping the Friday night bar scene for a few months? Maybe this means getting takeout for the family every Sunday night so you can spend your evening on your career change? You might also try to postpone a trip that will be right in the middle of when you expect to start interviewing. Or it might mean you need to step back from a volunteer commitment for the next quarter or two. 

      2. Try not to view this as a punishment. This is a strategic choice you’re making to give yourself the necessary time to make this pivot successfully.

  3. Have the conversations you need to have

    • Once you’ve identified what you need to succeed, you need to ensure that key members of your support network are aware of the choices you’re pursuing. 

    • Tell the Fri night crowd not to tempt you for a few weeks - but that you’ll celebrate with them once you get the new gig. Talk to your partner/family and ensure they are on-board with this potential change. Seek out advice if you’re not sure whether you’ve estimated your timing correctly. 

    • All of these conversations help you to gather the support you’ll need to slog through when you get frustrated. And admitting to these trusted folks that you’re looking to make a change makes it easier to start having the future networking conversations too.

  4. Put it on the calendar

    • For me, nothing happens if it doesn’t appear on my calendar. Partly because I need the reminders, but partly because I’ve told myself that I’m dedicating a specific amount of time on a specific day and time to work on a project. 

    • Add recurring appointments to your calendar to remind yourself to work on items related to this career pivot into tech. This is your commitment to yourself that you will make this happen. 

You might be thinking these items are obvious, but humans tend to resist change, even when you do actually want the change to happen. These steps might only take 20-30 minutes but it’s surprising how important they are for long-term career change success. 


Pivoting into a new career can be hard, depending on how BIG the move that you’re making is and how much support you have in making the move.

If you’d like some help with charting out your pivot into tech and you’d like to work with a small cohort of peers making this shift, please consider joining the Digital Orchards Fellowship waitlist: digitalorchards.com/fellowship