Nerd Journey: Career Advice for the Technology Professional

A Podcast to Help the Technology Professional Accelerate Career Progression, Increase Job Satisfaction, and Be more Effective in Their Current Role

Author: John White Nick Korte

Are you a technology professional unsatisfied with your current role? Looking for a resource to help understand changing job functions, changing organizations, or gaining recognition and progression? The Nerd Journey podcast helps explore alternative roles, increase job satisfaction, and accelerate career progression. Each week, we uncover patterns of technical career progression by dissecting careers of guests and discussing different job roles theyve held, or discussing relevant career topics. Weve interviewed people in IT operations, sales engineering, technical marketing, product management, people management, network engineering, cybersecurity, software development, entrepreneurs, and more. We also discuss improving job satisfaction and accelerating career growth. We are John White and Nick Korte, two technologists with experience in IT operations and sales engineering who started this podcast in 2018. We release on Tuesdays, and can be found at https://nerd-journey.com.
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Mind the Gaps: Organizational Changes and Your Career Lifecycle with Ryan Conley
Tuesday, 13 January, 2026

Has organizational change redefined your job role? If it hasn’t yet, it will at some point. Whether acknowledged or ignored, every organizational change at a company impacts you. This is broader than just layoffs and more employees under a single manager. What are the organizational changes we might see, and what can we do to stand out and stay the course? This week in episode 355 we’re joined by guest Ryan Conley. Listen closely as we uncover different patterns of organizational change and provide practical tips to take action when those changes happen. Ryan helps us understand the corporate lifecycle and how to reframe this concept to understand where we are in the career lifecycle. You’ll hear from Ryan’s personal experience why the most resilient (and successful) technologists can identify and fill the gaps left after an organizational change whether that means working for a new boss, joining a different team, or changing job roles. Original Recording Date: 11-13-2025 Topics – Framing Our Focus on Organizational Change, Observations and Patterns, Defining the Career Lifecycle, When Colleagues Leave the Company, Layoff Resources, Working for a New Boss, Becoming Part of a Different Team, Shifting Job Roles or Job Level Changes, Parting Thoughts 2:58 – Framing Our Focus on Organizational Change Ryan Conley is a global field principal with 11p years of technical pre-sales experience. Before this, Ryan accumulated 13 years of systems administration in industries like education, finance, and consulting. In a recent episode of our show, guest Milin Desai compared organizations to living, breathing organisms that change. Nick posits that we don’t always think changes at our company will or can affect us as employees, but they do. Ryan references Aswath Damodaran’s writings about organizational change through the frame of a corporate lifecycle. We can relate by considering where our company might be in that lifecycle. As we experience the impacts of organizational change, Ryan encourages us to consider where we are in our career lifecycle. 4:19 – Observations and Patterns We see organizational change in different ways. What are some of the things Ryan has seen that he would classify as organizational changes? Let’s take a step back, past the current headlines, and look at the wider industry. Companies are growing inorganically (through mergers and acquisitions) or organically through investments in R&D (research and development), for example. Ryan has worked with companies that grew by acquiring 2 new companies each year to give an example. When you’re on the IT side of the acquiring company, there is a lot involved in the process like integrating e-mail systems, networks, and CRM systems. This process also involves getting 2 teams to work together. If one team needs to move from Office 365 to Gmail, it can be a big adjustment to employees’ daily workflow. The acquiring and acquired companies may have the same or very different cultures. In some cases, a company will want to acquire others with similar cultures, while some may not be concerned about the culture and choose to focus on the intellectual property (products or services, knowledge of how to build or manufacture something, etc.) of the company to be acquired. Nick says the experience for people on the side of the acquiring company and that of the company getting acquired can be quite different. Nick worked in IT for a manufacturing company for about 9 years, and over the course of his time there saw the company acquire several other companies. Nick usually had to go assess technology systems of companies that were going to be acquired and figure out how to integrate the systems in a way that would best service the user base. From what Nick has seen, some employees from the acquired company were integrated into the acquiring company, while others were eventually no longer with the company. Anxiety levels about an acquisition may be different depending on whether you work for the acquiring company or the acquired company. “The people are just as much of the intellectual property of the company as, in many cases, the actual assets themselves. And in some cases, that culture just isn’t a fit.” – Ryan Conley Ryan shares the example of someone he knew who left after another company acquired their employer because the culture was not a fit. Losing a key leader or a key subject matter expert after an acquisition could create a retention problem because others may want to follow them or start looking elsewhere. "So how do you protect the culture internally? How do you integrate a different culture in? But also, how do you kind of protect the long-term viability of the team as individuals, first and foremost, but then also the organization long-term? Depending on the intellectual property the acquiring company is after, we don’t usually know the level of due diligence completed to understand the key resources or subject matter experts who must be retained for longer-term success. Ryan encourages to imagine being the CTO or VP of Research and Development at a specific company that is suddenly acquired. People in these roles drive the direction of the technology investment for their company today as well as years to come. After being acquired, these people might be asked to work in lower levels of leadership with different titles, which could result in “title shock” and require some humility to accept. This scenario is a leadership change that happens as a result of an acquisition, but we might see leadership changes outside of acquisitions. Some leadership positions get created because of a specific need, others are eliminated for specific reasons, and some get shifted down or changed. Each of these changes has a downstream impact on individual contributors. Ryan talks about the positive impacts of leadership changes and gives the example of when a former manager was promoted to senior manager and allowed that person to hire a manager underneath him. There isn’t always internal mobility, but leadership changes could create these opportunities for individuals. Nick talks about the potential impact of a change in our direct boss / manager. If a boss who was difficult to work for leaves the company, getting a different boss could make a huge positive impact on our daily work lives. Similarly, we might have a great boss leave the company or take a different role, requiring that we learn to work for someone else who may operate very differently. Ryan tells us he has worked for some amazing leaders and says a leader is not the same as a manager. Ryan cites an example of getting promoted into a role that allowed him to have more strategic conversations about the focus of a team with his boss. We can choose to mentor members of our team so that when opportunities arise from structural change, they are equipped to seize those opportunities. Change can be viewed as an opportunity. A company’s overall priorities may have changed. Shifting priorities may require a company to operate very differently than it has in the past, which can cause changes to people, processes, and technology. Nick references a conversation with Milin Desai on constrained planning from Episode 351. Milin encourages regularly asking the question “is this still how we want to operate?” The way a company or team operated in the past may not be the best way to do it in the future. Changes to operations may or may not create opportunities for our career. Ryan loves this mindset of reassessing, which could apply to the company, a team, a business unit, the technology decision, etc. “I love the mindset of ‘what was best, why did we do it, and why was it best then?’ And then the follow up question is ‘is that still best today?’ And it’s ok if the answer is no because that leads to the next question – ‘how should we be doing it today…and why?’” – Ryan Conley, commenting on Milin Desai’s concept of constrained planning Ryan talks about companies reassessing their core focus. We’ve seen some companies divest out of a particular space, for example. Nick says this reassessment could result in a decision to pursue an emerging market which could lead to the creation of a new business unit and new jobs / opportunities for people. It could also go in the other direction where the company decides to shut down an entire business unit. 15:30 – Defining the Career Lifecycle Going back to the analogy Ryan shared about corporate lifecycle, we can reframe this and look at the career lifecycle. “Where are you at in your individual career journey? Where are you at in that lifecycle?” – Ryan Conley People close to retirement may be laser focused on doing well in their current role and hesitant to make a change. Others earlier in the career may want to do more, go deeper, or be more open to making a change. Ryan recounts speaking to a peer who is working on a master’s degree in AI. “With challenge comes opportunity, so do you want to try something new? And it’s ok if the answer’s no. But if there is an opportunity to try something new and you’re willing to invest in yourself and in your company, I think that’s worth considering.” – Ryan Conley We’ve talked to a number of former guests who got in on a technology wave at just the right time, which led to new opportunities and an entirely new career trajectory. Becoming aware of and developing expertise in emerging technologies can lead to new opportunities within your company (i.e. being able to influence the use of that technology within your company). “I think as technologists, whether you’re a business leader over technology, whether you’re day in / day out in technology as an individual contributor…emerging technology brings new challenges, just with a learning curve…. There’s hard skills that have to be learned. You get beyond the education it’s then also sharing with the peers around you…. So, what was best yesterday? Is it still best today? And tomorrow, we’ll ask the question again.” – Ryan Conley Ryan says this goes back to our analogy. Should we be doing certain things manually now, or is it better to rely on tools that can help automate the process? If we go back for a second to Ryan’s previous mention of integrating the technology stack for different companies, being part of the integration process might enable someone to learn an entire new technology stack. We might have to assess what is best between Google Workspace and Microsoft 365, for example, and develop the transition plan to move from one to the other and perhaps even capture the business case for using both within a company. To Ryan, this is an example of seeing a problem or gap and working to fill it. “If you want to be just a long-standing contributor to the team and your individual organization, I think it’s worth calling out…those who stick around longer and get promoted faster are the ones who see a gap and they plug it.” – Ryan Conley Ryan shares a personal story about a co-worker who attended a Microsoft conference on their own dime. This person worked over a weekend to setup a solution that saved the team significant time doing desktop imaging. But then, Ryan’s colleague took it a step further and trained the team on how to use it. Nick highlights the fact that we should remember to document our accomplishments to keep track of how we’ve changed as a result. We can use this information when searching for new opportunities or even in conversations with our leader. 20:34 – When Colleagues Leave the Company Another form of organizational change we’ve seen is outsourcing specific business functions. Daniel Paluszek spoke about companies outsourcing functions outside of their core business in Episode 338. If IT is outside the core business, a company might decide to outsource it. It doesn’t mean that’s the right decision, but it could be a possibility. Companies may outsource other functions like HR and payroll as well to give other examples. If IT was internal and it gets outsourced, that is an organizational change and will affect some people. Similarly, insourcing a function which was previously outsourced will have an impact. Ryan has learned in the last few years that some people are more adaptable to change than others. “And it’s not just looking at the silver lining. It’s recognizing the change. Maybe there’s a why, and maybe there isn’t a why. Or maybe the why hasn’t been clearly articulated to you. Being able to understand, what does this mean to me…. As an organization do I still believe in them? Do I still believe in the technology as a technologist? Do I still enjoy the people I work with? Those are all questions that come up, but ultimately you have to decide…is this change I want to roll with? Is this change I don’t want to roll with?” – Ryan Conley To illustrate, Ryan gives the example of a peer who left an organization after seeing a change they didn’t like in order to shift the focus of their role from technology operations to more of a site reliability engineering focus. While this type of change that results in a talented individual leaving an organization can be difficult for teammates to accept and for a manager to backfill, these types of changes that are beneficial to someone’s career should be celebrated. When we assess whether the changes made at a company are those we can accept and roll with, we can first make sure we understand what we are to focus on as individuals operating within the organization. We have an opportunity to relay that to other members of our team for the benefit of the overall team culture and to build up those who do not adapt to change well. Understanding organizational changes and what they mean for individuals may take repetition. While Ryan understands that he responds well to change, he remains empathetic to those folks to need to hear the message a few times to fully understand. Nick says we can learn from the circumstances surrounding someone leaving the company. For those we know, what interested them about taking a role at another company? Perhaps they took a role you’ve never thought about for yourself that could be something you pursue in the future. If a member of your team leaves the company, sometimes their role gets backfilled, and other times it may not. If the role is backfilled, you get to learn from a new team member. If not, the responsibilities of the departing team member will likely be divided among other team members. Though it would result in extra work, you could ask to take on the responsibility that would both increase your skill set and make you more valuable to the company. When Ryan worked for a hedge fund, the senior vice president left the company. This person was managing the company’s backups. Ryan had experience in this area from a previous role at a consulting firm and volunteered to do it. Shortly after taking on this responsibility for backups, he found that restoring backups from tape and needing to order new servers posed a huge risk to the company in a disaster scenario (i.e. would take weeks to restore everything). Ryan was able to write up a business plan to address the business continuity risk and got it approved by the COO. “Being able to see a gap and fill it is the central theme, and that came from change.” – Ryan Conley Ryan says if you’re willing to do a little more work, it is worth the effort to see a gap and work to fill it. 27:34 – Layoff Resources We acknowledged some of the byproducts of organizational change like layoffs and flatter organizations in the beginning of our discussion. We are not sidestepping the fact that layoffs happen, but that is not the primary focus of our discussion today. Here are a few things that may help if you find yourself being impacted by a layoff: First, know that you are not alone in experiencing this. “When a layoff hits, it’s important to remember…it’s extremely rare that that’s going to be personal. Once it’s firmly accepted, look for the opportunity in a forced career change. It’s there.” – thought shared with us by Megan Wills Check out our Layoff Resources Page to find some of the most impactful conversations on the topic of layoffs on our show to date. We also have our Career Uncertainty Action Guide with a checklist of the 5 pillars of career resilience as well as reusable AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed. 28:43 – Working for a New Boss Let’s move on to section 2 of our discussion. If you’re still at a company after an organization change has happened, we want to talk through some of the ways you can take control, take action, and succeed. We want to share a thought from former guest Daniel Lemire as we begin this discussion: “Companies are the most complicated machine man has ever built. We build great machines to accomplish as set of goals, objectives, or outputs. The better you can understand the value the company delivers…the faster you can understand where you fit in that equation. If you don’t understand where you contribute to that value, there’s work to be done. That work may be on you, may be on your skills, or perhaps it’s your understanding of where you fit into that equation.” – Daniel Lemire Let’s say that you’re impacted by an organizational change and will be working for a new boss. What can we control, and how to we make a positive impact? Ryan says we can be an asset to the team and support larger business goals by first giving some thought to who the new boss is as a person. Try to get to know them on a personal level. Ryan wants to get to know a new boss and be able to ask them difficult questions. Similarly, he wants a boss to be able to ask him difficult questions. Meeting a new boss face-to-face is ideal if that is possible, but this can be more difficult to arrange if your boss lives a large distance from you. Make sure you understand the larger organization’s mission statement. As individual contributors, we may lose sight of this over time. “If that is important to the team and the culture, I think it’s worth making sure you’re aligned with that. I think it’s worth understanding your direct manager’s alignment toward that and then having that kind of fuel the discussions…. What are you expecting of me? Here are my expectations of you as my manager. Where do you see change in the next 6, 12, 18 months?” – Ryan Conley, on using mission to drive conversations with your manager A manager may not have all the answers to your questions. They could also be inheriting a new team. Ryan encourages us to ask how we can help our manager to develop the working relationship further. This is something he learned from a previous boss who would close every 1-1 with “is there anything else I can do to help?” Nick says a manager may be able to contextualize the organization’s mission statement for the team and its members better than we can do for ourselves. For example, the mission and focus of the team may have changed from what it once was. A new manager should (and likely will) set the tone. Nick would classify Ryan’s suggestions above as seeking to learn and understand how your new manager operates. Back in Episode 84 guest Brad Pinkston talked about the importance of wanting to know how his manager likes to communicate and be communicated with. This is about understanding your manager’s communication preferences and can in some ways help set expectations. A manager may be brief when responding to text messages, for example, because they are in a lot of meetings. But if they tell you this ahead of time, it removes some assumptions about any hidden meanings in the response. Ryan gives the example of an executive who used to respond with Y for yes and N for no to e-mails when answering questions. We can also do research on a new boss in advance. We can look on LinkedIn to understand the person’s background and work history. We can speak to other people inside the company to see what they know about the person. Ideally, get a perspective from someone who has worked for the manager in the past because a former direct report might be able to share some of the context about communication preferences and other lessons learned from working with that specific manager. We can also try to be mindful of how the manager’s position may have changed due to organizational flattening. They may have moved from managing managers to having 15 direct reports who are individual contributors, for example. “Their time might be stretched thinner, and they’re just trying to navigate this new leadership organizational change with you.” – Ryan Conley The manager may or may not have wanted the situation they are currently in. How is your boss measured by their boss, and how can you help them hit those metrics? You may not want to ask this in the first 1-1, but you should ask. Ryan suggests asking your boss what success looks like in their role. You can also ask what success for the team looks like in a year and what it will take to get there. Based on the answer, it might mean less 1-1s but more in depth each time, more independence than you want, or even more responsibility than you wanted or expected. Ultimately, by asking these questions, you’re trying to help the team be more successful. We want our manager to understand that we are a competent member of the team. Understanding what success looks like allows us to communicate with our manager in a way that demonstrates we are doing a good job. Some of the time in our 1-1s with a manager will be spent communicating the things we have completed or on which we are actively working. We need to demonstrate our ability to meet deadlines, for example. Daniel Lemire shared this book recommendation with us – The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter. It’s a great resource for new leaders but also excellent for individual contributors. Ryan tells us to keep track of our wins over the course of any given year (something that was taught to him) so we have it ready for performance reviews. He encourages keeping a journal that we start in January. Keep track not only of what you did but the outcomes your work delivered and the success metrics. For example, if you gave a presentation, note the number of people present. The company culture may have some impact on the language you need to use to word your accomplishments (i.e. using “I” statements). “I didn’t want to be the only person who could do it. I’d rather learn it and then enable 5 other people to do it. And then those 5 people go do it, and that is a much bigger outcome.” – Ryan Conley, on the outcome of efforts at work and being a force multiplier Have a journal of the things you do at work that you update consistently. This could be screenshots, a written description, etc. “What are the metrics that you should be tracking? Mentally think about that because…when you have your annual review, you’re going to miss something. You’re going to miss a detail. You’re going to miss an entire line item versus if you started in January and you just get into the practice of ‘I did this.’ And then when you’re having your first annual review with this brand-new manager, it’s far easier to have a more successful conversation.” – Ryan Conley, on the importance of documenting our work in a journal somewhere Ryan reminds us it is ok to use generative AI tools to check our work. Use multiple different tools to get suggestions on how you might want to phrase the outcomes you delivered and the metrics you tracked. Nick says we should document our accomplishments as Ryan mentioned, but we should make sure we keep a copy of them so that we do not need to rewrite them from nothing in the event we are impacted by a layoff. If the journal containing all of your accomplishments is sitting in the corporate OneDrive or cloud storage, you will lose access to it when you leave the company. Be sure you have a disaster recovery plan for your accomplishments! The new boss is probably going to have team calls of some kind. While what you experience may vary from this, in Nick’s experience the first time a manager hosts a call with their team they will share some career background, how they operate, and give team members some idea of what to expect. This kickoff team call usually happens before 1-1s begin. Listen really carefully when this first team call happens. Write down some questions you can ask the boss in that first 1-1 conversation. The manager will have to lead that first 1-1 conversation a little bit, but coming into it prepared with questions will be far easier than trying to think of questions in the moment. A simple follow up question Ryan suggests is how the manager wants to handle time off. Is there a shared team calendar, a formal process, carte blanche, specific blackout dates to be aware of, etc.? We can handle the simple things about how this new manager operates and what their values are early on in our working relationship. Ryan tells us he learned far too late to ask how managers handle promotion / raise / career growth conversations. One of Ryan’s past managers scheduled a quarterly checkpoint to specifically talk about career growth items. Ryan was in charge of making the agenda in advance, and his manager would come prepared to talk about each agenda item. It’s ok to ask for these regular career discussions. If your manager has a large team, these may be less frequent than otherwise. Ask the manager about the best way for both you and them to come into these discussions prepared. Nick likes the idea of an individual owning the agenda for these conversations. Nick tells us about a manager who sent out 1-1s to team members and provided a menu of options for the types of things that could be discussed during the 1-1 time in the body of the meeting invitation. It helps give people ideas for things to discuss but also lets them know the overall intention of the 1-1s. For the very busy manager, we could ask to use a specific 1-1 to talk about career-related items rather than in a separate meeting (if needed). Nick mentions a recent episode of Unicorns in the Breakroom Podcast in which Amy Lewis talks about using a shared document for 1-1s to hold an employee accountable for bringing agenda items and to document what transpired in previous conversations. Along the lines of trying to be helpful to a new manager, ask how they want to handle team calls when on vacation. Will team calls be cancelled when the manager is on vacation, or are they looking for team member volunteers to host these calls? This may be an opportunity to step up and do more if you want that, especially if you want to gain some leadership experience. Ryan tells us at one point he was a team lead, and part of his responsibility was leading team calls in his manager’s absence. This involved leading the call, taking notes, and taking action on follow up items from the meeting. We should bring up time sensitive items to the boss quickly, especially if something needs attention. Communicate things that have a financial impact to the company (a subscription renewal, drop dead due date to exit a datacenter facility, point at which access to something will be lost, etc.). Do not assume your manager knows if you are unsure! Ryan recounts a story from earlier in his career when a CFO wanted a specific number of users added to the Exchange server. There were several cascading impacts of completing this task that went well beyond the scope of licensing and involved procuring more hardware. Ryan took the time to explain the implications. “This is a simple ask. You want the answer to be yes, but I’m going to give you more context…. There is a deadline. I want to make sure we hit it as a team, but there are some implications to your ask. I want to make sure you’re fully aware.” – Ryan Conley, on giving more context to leadership Share what you have in flight and the priorities of those items. The new manager may want you to change the priority level on some things. 45:21 – Becoming Part of a Different Team You could end up working on a completely different team of peers as a result of organizational change. You might work on the same team as people you already know but might not. You may or may not work for the same boss. Ryan and Nick have experienced very large reorganization events and ended up in different divisions than they were previously. Ryan had a change of manager, change of a peer he worked closely with, and joined a new team of individuals reporting up to the same boss all at once. “A little bit of the tough lesson is you go into a bigger pond…. I think it’s ok to take a moment and pause. For me, I had to kind of reassess and kind of figure out…what are these changes? What are the new best ways to operate within this new division so to speak? …within my team, no one on my prior team was on my team, so it was like this whole new world.” – Ryan Conley After this change, Ryan saw an opportunity to go deeper into technology and chose to take a different role. Ryan worked for a new (to Ryan at least) leader who was very supportive of his career goals. This leader helped Ryan through the change of roles. “If you do good work, even through change…if you’re identifying gaps, you’re filling it, you’re stepping up where the team needs you to step up, you’re aligning with the business direction to stay focused…I think there can still be good outcomes even if in the interim period you’re not 100% happy.” – Ryan Conley If you don’t know anyone on your new team, you have an entire set of people from which you can now learn. Does your job function change as a result of joining this new team? Make sure you understand your role and its delineation from other roles. Maybe you serve larger customers or work on different kinds of projects. Maybe you support the technology needs of a specific business unit rather than what we might deem as working in corporate IT. Maybe you focus on storage and high-level architecture rather than only virtualization. It could be a chance to learn and go deeper in new areas. Did the focus of the overall team change (which can trickle down and impact your job function)? Maybe you’re part of a technology team that primarily manages the outsourced pieces of the technology stack for your company. So instead of working with just employees of your company you now work with consulting firms and external vendors. Ryan says we can still be intentional about relationships and he illustrates the necessary intentionality with the story behind his pursuit of a new role. Ryan was intentional about his desire to join a new team after the reorganization, but it didn’t work out on the timeline he wanted. He remained patient and in constant, transparent communication with a specific leader who would eventually advocate for him with the hiring manager. Just doing our job can be difficult when we’re in a challenging situation like a manager we do not get along with, trying to evolve with a top-level strategy change, etc. This can involve internal politics. Stay the course. Ryan tells us about a lesson he learned when interviewing for a new role he wanted. “Maybe be a little bit more vocal. Pat yourself on the back in a concise way. Again…go back to your journal, know your metrics, and stick by them.” – Ryan Conley, on interviewing and humility Nick says the intentionality behind building relationships applies to your relationship with your boss (a new boss or your current boss that has not changed). This also applies to new teammates! What are the strengths in the people you see around you? Who volunteers to help? Who asks questions when others will not? Ryan shares a story about 2 peers who on the surface seemed to disagree a lot but ended up making each other better (and smarter) by often taking opposing sides on a topic. When one of them left the company, the other person missed getting that perspective and intellectual challenge. Ryan suggests we pay attention to the personalities of team members and the kinds of questions they ask. If a specific teammate tends to do all the talking in meetings, find ways to enable others to speak up who have valuable perspectives but may be quieter. This at its heart is about upleveling others. We can do that when we join a new team, but we can also do this for former teammates by keeping in touch with them over time. This could apply to former teammates who still work at the same company as well as those who have left the company. Ryan tells us a story about when he first made the transition from working in IT operations to getting hired at a technology vendor in a very different role. “It’s very different being face-to-face as a consultant, face-to-face as a vendor. And I had a buddy. He started going back 11 years almost to the day here. We were each other’s lifeline…. He would have a bad day, and he would call me. Most of the time I was just there to listen…. And then the next week it was my turn, and I would call him…. So having a buddy in these change situations I think is a great piece of advice.” – Ryan Conley It can be easy to fall out of touch with people we no longer interact with on a daily or weekly basis. This takes some effort. We’ve met people who try to setup a 1-1 with someone in their professional network once every 1-2 weeks. Ryan has a tremendous amount of empathy for others who have recently had a child, for example. We can buddy up with specific professional or life experience and take the opportunity to learn from them. Ryan refers to building an “alumni network” of people you want to remain close with over time. While this helps build our own set of professional connections, we can do this by mentoring others as well (a chance to give back, which is usually much less of a time commitment than we think). Ryan has mentored a number of new college graduates and managed to keep up with their progress over time. Listen to the way he describes the career progression of his mentees and the long-term relationships it produced. We might be mentoring others (on our own team or beyond). This could act as relatable experience for a future role as a team lead or people manager, but highlighting this experience to your manager is something you should do in those career conversations. In those 1-1s with your manager you are asking how you are doing but also how you can do better. Sometimes that means doing more of something you have done in the past. Ryan reminds us that the journal is a tracking mechanism for specific actions and their impact. Whether it’s mentoring or helping the manager with hiring or candidate evaluation, be sure to track it! There might be a gap in expertise on your team that you can fill (either because you have a specific skill or because you learned a new skill to fill that gap). When joining a new team, do some observing and stay humble before you declare there is a gap and that you are the one to fill it. Ryan says we can raise gaps with our manager. For example, maybe there is only one person on the team who knows how to do something. Could you pair with that person and cover them while they are on vacation? “I think it goes back to recognizing that you cannot learn it all and then revaluating…what do I need to learn? So, there’s certain functions that you have to know how to do, and that’s where your manager’s going to help you set those expectations…. We’re in technology, so as a technologist, what do you want to learn? What do you want to do more of? And that could be a gap that you see, and you have that conversation….” – Ryan Conley If there is not an opportunity at work to learn what you want to learn (i.e. your manager might not support you doing more of specific work, etc.), you can learn it on your own time and then re-evaluate longer term what you want to do. 59:46 – Shifting Job Roles or Job Level Changes We talked about this a little bit earlier. Maybe you stay an individual contributor, move into leadership, or change leadership levels entirely within an organization. Ryan talks about the new expectations when you change your daily role. There are expectations we put on ourselves and those expectations put on us by our leaders. There are both opportunities and challenges. Ryan shares that he has been approached in the past to lead a team, but when this has happened, he took the time to think through what he wanted (his career ladder, his motivations, and his desired focus). “Leading people is not something that I want to currently focus on. I know what I’m motivated by. I’m a technologist at heart. I want to keep learning, and I personally like the technology that I’m focused on right now. And it’s not that leadership would necessarily remove technology entirely…. It’s just it would be a different focus area. And I think in your career journey it’s worth just kind of keeping tabs on where you’re at in your career (the ladder of change that we keep mentioning, that lifecycle)…. Do you want to go up the ladder as part of your lifecycle and get into a management role? I think mentorship can be very fulfilling. I think leading people can be very fulfilling. But in my case, I’ve decided I still want to stay an individual contributor. There’s still aspirations that I have there….It’s ok to say no is really what I’m getting at…. Really think about the job that you’re in at the company that you’re in. What are the opportunities within? What motivates you? And stay true to that.” – Ryan Conley Ryan has said no to being a people leader as well as to technical marketing roles. He had a desire to get through the principal program. He encourages listeners to think about whether they would be happy in 1-2 years if they took a new role before making the final decision. Nick mentions the above is excellent when you have the choice to take a new role. But what if it’s forced on you as the result of an organizational change? We can recognize where we are in the career lifecycle even if an organizational change places us in a new role that was not our choice. Make sure you understand what the new role is, and think about how you can align it with where you are in the career lifecycle (including the goals you have and the things you want). Nick had a manager who encouraged his team to align their overall life purpose to the current job role or assignment. In doing this, it will be easier to prevent intertwining your identity with your job or your company. We may have to put out heads down and just do the work for a while. But maybe there is an opportunity to align with the things you want and the type of work you want to do which is not immediately obvious. In this job market, if you are employed, be thankful and do a great job. Ryan hopes listeners can think back to an unexpected change that happened which led to new opportunities later. “Pause, recollect, align your focus with your new manager, align your focus with either the changing mission statement or the current mission statement…. What is fulfilling you personally (your own internal values)? If they are being conflicted, I think there’s a greater answer to some of your challenges, but they’re not being conflicted how can you be your best self in a company without the company being all of yourself? …The cultural identity of the workplace and the home can sometimes be a little too close, a little to intertwined…. Maybe you’re just way too emotionally invested in your day job and it’s just a good moment to reset…. What is your value system? Why? And then how can you be your best self in your workplace? And I think far too often we want to have our dream job…. ‘A dream job is still a job. There are going to be days when it is just a really difficult day because it’s a really difficult job. It’s still your dream job, but every job is going to have a difficult day.’” – Ryan Conley Every job will be impacted by some kind of organizational change multiple times throughout your career. 1:06:18 – Parting Thoughts Ryan closes with a funny anecdote about a person who worked on the same team as him that he never had the chance to meet in person. In this case, the person invested more in their former team than meeting members of their new team. Maybe a good interview question for those seeking new roles could be something about organizational changes and how often they are happening at the company. Ryan encourages us to lead with empathy in this job market and consider how we can help others in our network who may be seeking new roles. Ryan likes to share job alerts on LinkedIn and mentions it has been great to see the formation of alumni groups. “Share your rolodex. Help people connect the dots. And lead with empathy.” – Ryan Conley To follow up on this conversation with Ryan, contact him on LinkedIn. Mentioned in the Outro A special thanks to former guest Daniel Lemire and listener Megan Wills for sharing thoughts on organizational change that we were able to include in this episode! Ryan told us we can lead with empathy when helping others looking for work in this job market, but Nick thinks it’s empathy at work when we’re asking a new boss or team member how we can help. If you want to bring more empathy to the workplace, check out Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3) in which guest Marni Coffey tells us about empathy as her greatest skill. It’s full of excellent examples. If you’re looking for other guest experiences with organizational change, here are some recommended episodes: Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2) – Shailvi talks about a forced change of role that was actually an opportunity in disguise Episode 168 – Hired and Acquired with Mike Wood (1/2) – Mike Wood’s company was acquired, and the amount of travel went up soon after to increase his stress. Episode 169 – A Thoughtful Personal Sabbatical with Mike Wood (2/2) – Mike Wood shares another acquisition story that this time ended with him taking a sabbatical. Episode 84 -Management Interviews and Transitions with Brad Pinkston – Brad Pinkston shares what he likes to do when working for a new boss. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: nerdjourneypodcast@gmail.com DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.