Welcome to episode 244 of the Nerd Journey Podcast [@NerdJourney]! We’re John White (@vJourneyman) and Nick Korte (@NetworkNerd_) – two technology professionals with backgrounds in IT Operations and Sales Engineering on a mission to help others accelerate career progression and increase job satisfaction by bringing listeners the advice we wish we’d been given earlier in our careers. In today’s episode we share part 2 of an interview with Tim Crawford, talking through how to determine if pursuing management makes sense for a person, how to better communicate with executive leaders, thoughts on executives progressing to the board of directors, coaching as a form of teaching, and how to decide what’s next in your career.

Original Recording Date: 09-01-2023

Tim Crawford is founder and CIO Strategic Advisor with an advisory services and research firm called AVOA. You can find part one of our interview with Tim in Episode 243.

Topics – A Choice of Interest and Priority, Communicating with Executive Leaders, Teaching and Coaching as a Way to Give Back, Deciding What’s Next

3:50 – A Choice of Interest and Priority

• Is leadership about choosing to follow the greater interest (people or technology)?
  • This was hard for Tim, especially since he started out in technology.
  • Tim says at some point we need to give up the technology and recognize we are a leader.
  • Tim had a boss who told him once, “my job is to deliver an organization.” At the time he did not really understand what it means.
  • Tim is still learning today what it means to be a leader and feels we should all be looking for ways to continually better ourselves.
  • As one progresses down the leadership path, there is an eventual realization that you can only do so much hands on work. A balance must be struck between leading the organization and being hands on with the technology.
  • Tim gives the example of a manager having an opening on a team but keeps fixing technology problems on their own.
  • “It really comes down to that balance and then what you’re prioritizing. Are you prioritizing being a leader or the technology? If it’s the technology that drives you, then maybe leadership is not your interest, and that’s ok too. We need individual contributors as much as we need leaders.” – Tim Crawford, on decisions to be in leadership
  • The highest level leader (or ultimate level) is serving on a board of directors and being part of a governance body (and not an operational body). The way you communicate and what you communicate has to be different than what it was in previous roles.
  • At some point, we make the choice as to whether we are interested in leadership and people or technology. Tim remembers going through this at multiple times over the course of his career (finding he was more interested in leadership than technology). It isn’t just a single point in time where you make this decision and never look back.

7:32 – Communicating with Executive Leaders

• Tim says this is a challenge, citing he had given a presentation to some CDOs (Chief Digital Officers) and at other times CIOs (Chief Information Officers) on how to ascend to the board of directors.
• While many of us think we need to progress up and out of our current role, we need to remember to ask if that progression is really what we want or where we want to be.
• The presentation Tim gave to senior executives was to help them understand how a board of directors work, what it’s like, what they are interested in, how to interact with a board, how to get invited to a board meeting, some of the personas that often sit on boards, what to talk about in a meeting and how to present it, etc.
  • “Even at an executive level they may not have exposure to their board….I know CIOs from publicly traded companies that do not have access to their board.” – Tim Crawford, on tech executives and access to the board of directors
  • The advice Tim gave to the group of executives is the same that he would give to the most junior person – “understand your business.”
  • The language of business is more than just money. We need to understand how our companies make money and how they spend money.
  • Tim gives an example of a clothing manufacturer (GAP).
    • Customers can engage with the company through a website, by visiting a company store, by using a mobile app, or even through buying merchandise secondhand. This is how the company makes money.
    • GAP doesn’t make its own clothing and would work with contract manufacturers in other countries who build the designs GAP creates. These products then have to be shipped and distributed to stores or to customers. This is where the business would spend money.
  • Good places to learn about how a company spends and makes money are by looking at its financial reports. The big 3 as Tim calls them are as follows:
    • The income statement
    • The cash flow statement
    • The balance sheet
    • A 4th component could be earnings and owner’s equity
  • The big 3 say a lot about a publicly traded company. Even if you cannot read them all at a deep level, it allows you to see where risks and opportunities for the company are.
    • Look at what you’re doing in your daily work and think about how it connects to what you see in the financial reports.
    • It’s important to understand how what we do in our role creates value for the company in line with the objectives in the financial statements (set by board of directors). Tim says understanding how to connect those dots is a huge step forward.
  • It isn’t just junior level folks who struggle with connecting these. Even more senior personnel struggle here. Over time one can learn a little more.
    • “What it also does is it causes you to sit in a meeting, and you start to hear things a little differently. You start to hear things that you didn’t notice before or maybe you tuned out of…It starts to inform you in a different way, and you become much more sophisticated in your thinking, which then just helps you advance your career.” – Tim Crawford, on how understanding financial statements and the business can help you progress
  • John mentions this is like watching a suspense movie and not understanding why characters act the way they did until the very end. When you watch the movie again you can see motivations leading to patterns of behavior.
  • Tim has been given feedback that he has the reputation of going into a contentious meeting and once it ends all parties seem to walk away with what they were looking for (and the situation is much less contentious).
    • Tim realized he was reading people’s body language in meetings and not just the things they said (which is harder to do on a remote session).
    • “You start to watch the body language of people, and you get a lot more information about what’s resonating and what’s not. It becomes really interesting when you’re trying to negotiate and make something work….These meetings are about negotiation. At the end of the day it’s about negotiation.” – Tim Crawford
    • We should pay attention to word choices people use and if they are different than what would normally be used. It’s an indicator.
    • The clues are something we can notice earlier as we go through our careers.
    • “But it’s important to keep your eyes open, your mouth shut, and your ears peaked.” – Tim Crawford, on paying attention to the body language and behaviors of others
    • Speaking in meetings should not be about who can talk the most but rather about who can provide the most value to the discussion, project, etc.
    • “It’s not the most air time. It’s the most insight.” – John White

17:42 – Teaching and Coaching as a Way to Give Back

• Sometimes it is not about you producing the answer. It may be helping someone else produce the answer (even if you know the answer).
  • Tim tells us this is a skill. And it is NOT manipulation. What you’re trying to do is help others see the path to buy into the outcome.
  • We need to strike a balance between speaking and not speaking / encouraging others to speak.
  • John says the skill we’re discussing is called coaching – evoking a realization, decision, behavior in someone.
    • “I’m realizing…leadership and management has in it a set of extremely technical skills that are almost orthogonal to the technology that is underlying those roles.” – John White
• Tim says we are exposed to leadership when we’re very young from our parents and from our teachers.
  • Teachers don’t generally provide the answer. They teach you how to work through a problem.
  • What Tim suggests is we’re teaching people how to work through the problem in meetings by coaching. We need other people to learn as well and not just be given the answer.
  • Tim says this goes back to community. We are gaining from and giving to the community.
    • “This is a way you can give to the community, by teaching them how to fend for themselves, how to work through a problem on their own. Don’t just give them the answer. Help them through it. And then the next time, they can work through the problem, and they don’t have to come to you with it. But the other thing is the next time they come to you it’s probably going to be a juicier problem that they’re stuck with. And that will be the next opportunity for you. So, it’s a cycle that you go through.” – Tim Crawford, on teaching as a way of giving back to community

21:14 – Deciding What’s Next

• How do we go about approaching what is next in our careers?

  • Tim says this requires a heart to heart with ourselves for which most people are not prepared. We need self-reflection and to understand our values / things that are important.
  • We must also be humble and realize we do not know everything.
  • Think about whether you’re really right for a role and if you’re ready for it.
  • Consider also…
    • Is this worth the risk to get what you want / what you’re looking for?
      • Think back to things you need to be successful to help here.
    • Is this just about a bigger paycheck or different title?
      • Perhaps this should not be the only thing we’re seeking.
  • Tim has told groups of CIOs seeking board level positions that not all are board level material and that they should be ok with it.
    • We need to understand what is and what is not really a fit for us. Mentors can really help here, no matter where we are in our career.
    • Are you the right persona that would be appropriate to sit in a board room and engage in a board meeting? Many IT people, including CIOs are not (may not be the right demeanor, may not have the right relationships to be invited in to the board).
  • Tim wanted the ability to affect companies and organizations at a completely different level, so serving on a board / as a board advisor is attractive.
    • A board advisor provides greater flexibility than a board director in terms of who you engage with.
  • “At the end of the day whether you’re the most junior person in IT or the most senior person in IT…relationships, knowing who you are, knowing the value you bring to the organization, understanding your business are all super critical….If you start there, that will take you a long way in the right direction to determine who you are, the value you bring, and where your place is as you go through that career ascension.” – Tim Crawford

• If you want to follow up on this conversation with Tim, you can reach him…

  • On AVOA’s website
  • On LinkedIn
  • On Twitter / X

• Mentioned in the outro

  • Tim mentioned the job of delivering an organization in one of our favorite all time episodes of the Datanauts podcast (hosted by former guests Chris Wahl and Ethan Banks) – Datanauts Episode 101.
    • John highlights that the product / output of managers at multiple levels is that high functioning organization.
  • Knowing the value you provide to an organization falls in line with the advice Don Jones gave in Episode 137 to think of yourself as a vendor who provides a service and knowing the problem you solve.
    • Knowing the value you provide can help you articulate it and show evidence of it in your next performance review or job interview.
  • We were surprised to hear that even high level executives did not have access to board of directors meetings. It’s great that we have folks like Tim to help people prepare for getting to that level.
    • We have shared advice before on knowing success metrics of your manager, but it’s a similar story when you move up from there. Are we taking the time to understand what success metrics exist for C-level executives?
    • Remember to go and read the financial reports, and maybe you can ask questions about these when you speak to executives.
    • John says we should do some research on who does the hiring / firing for executives and who usually does the performance management at a company. Find out who the CEO manages directly, for example.
  • Self-reflection for what’s next in your career takes the deep work and being bored we discussed previously (see Episode 144 for more on this).
    • Nick advocates for journaling here, and we discuss the morning pages discipline. It’s been mentioned in The Artist’s Way by Julia Cameron. See also Nick’s blog article on morning pages.

Contact us if you need help on the journey, and be sure to check out the Nerd Journey Podcast Knowledge Graph.