A CEO’s Approach to Product and Career Roadmaps with Todd Cochrane (2/2)

Welcome to episode 251 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 Todd Cochrane, detailing how his company works through product and service roadmaps collaboratively, how to keep employees engaged in their work, the challenges of being CEO, and thoughts on developing a strategy for emerging technologies like artificial intelligence.

Original Recording Date: 10-06-2023

Todd Cochrane is the founder and CEO of Blubrry Podcasting, a full service podcast hosting platform. If you missed part 1 of our discussion with Todd, check out Episode 250.

Topics – Filling Expertise Gaps, Corporate and Individual Roadmaps, Leadership and Employee Engagement, Developing a Useful AI Strategy

3:32 – Filling Expertise Gaps

  • Nick feels like the above experience is an iteration of being mindful of our gaps in knowledge just like when Todd got on his show and asked people with different expertise for help. It’s learning from others but also humility.
    • Todd says he was a high school graduate going into the Navy and didn’t get a degree until he had been in the Navy for 20 years. In a way he was getting credit for much of what he had learned via the school of hard knocks.
    • Todd has seen people fail because they hung out with others who may have been fun people but who just were not going to advance in a company. It’s important to surround ourselves with good people.
  • John points out that just like skills diversification when one is riding a technology wave, it’s also about having a diverse set of people around us whose experience we can call upon to fill gaps in our own expertise.
    • We cannot be experts in everything. Having access to others with different expertise can enable the kinds of pivots we spoke about earlier (for the individual or for a business).
    • As company owner and founder, Todd would rather collaboratively come up with a plan with his team than just give them a directive.
      • Todd calls himself a geek and says there are times where he wants something geeky (i.e. a feature) that 90% of his customers may not ever need. It’s important to be careful and prioritize for the 90%.
      • There are certainly times when Todd’s team are building a feature that is intended to promote adoption (i.e. building it for only a small subset of customers) like some of the podcasting 2.0 work they have done. But these occasions are pretty rare, and the team knows why they are building it.
    • Todd says the team are very cognizant of the products and services roadmap when making decisions, and he looks at the year’s roadmap every day. Every 2 weeks there is an oversight meeting to discuss the roadmap with other company leaders.
      • Priorities may need to change based on the marketplace conditions.
      • “You have to be careful. Because if you’re working Scrum…if you interrupt the cycle you could really do huge damage.” – Todd Cochrane, on being flexible in your product roadmaps

7:32 – Corporate and Individual Roadmaps

  • Nick posits that most of us do not have a roadmap for ourselves and our careers, nor do we look at it daily.
    • Todd says the roadmap is the company roadmap but might as well be his personal roadmap.
    • John emphasizes the company’s execution on a roadmap is analogous to a individual contributor’s view of themselves / their career as a product.
      • Excellence in what a company is doing today is of course important.
      • Companies often have innovation budgets to enable building products people might not know they need until they use it / can have it (i.e. the iPhone or perhaps certain podcast hosting features).
      • Maybe as individuals, in addition to excelling at what we do today (a baseline of excellence in execution), we should have our own innovation budget allotted for building new skills and learning about the next / current technology wave. This avoids us from being locked into excellence in only what we do today just like Todd’s company was able to shift away from being only a media intermediary in the early days.
    • Todd says his team is fully remote but does come together a couple of times per year for planning purposes (1 time in person, 1 time 6 months later remotely as a follow up to that).
      • These meetings are a chance to look at what is going well, what isn’t, and a chance to solicit new ideas.
      • During these discussions, teams criticize one another and give feedback. It is a very frank set of discussions that results in action items. Todd says they try to preserve people’s feelings during the discussions, but it is about honest evaluation of how things are going.
      • The above will be quite difficult for companies with more than 20 employees. Todd says the approach works well for his company.
      • Todd also tells us a bad apple (1 person) can make a very negative impact on the company. This person might not be staying current or is constantly fighting with others.
      • “Sometimes it’s better to cut those folks loose. Even though you think you shouldn’t, sometimes getting rid of that just maybe 1 person can completely change how a company’s atmosphere is and the flow and the speed….So I learned this late – that sometimes it’s just better to say ‘thank you for your work it’s time to part ways.’ It’s just like pivoting. Sometimes the employee mix needs to change.” – Todd Cochrane, on making difficult decisions around people
      • Todd says there was someone who left the company about a year ago, and the business had a complete transformation (in a good way) as a result.

12:00 – Leadership and Employee Engagement

  • Many people moving into leadership are not prepared for the hard personnel decisions. What are other challenges Todd has noticed as CEO, being in charge of the roadmap and the people?
    • Todd says he has been quite lucky with very little turnover, having only a couple of people leave the company over time and a couple of others get asked to leave. Overall the team has been strong (a possible sign they are doing something right).
    • “We all get bored if we’re doing the same thing, but we’re in a business where we can build new stuff all the time and have new challenges. So I think from my perspective…if you’re not innovating, then your employees are going to get bored, and they’re going to go some place that is innovating to give them a challenge.” – Todd Cochrane
    • Ideally Todd wants employees to feel their work is exciting, that it is making a difference, and for them to be excited to start work on it again each day.
    • In IT sometimes work is drudgery (or “the thunking” as Todd calls it) and is not something we enjoy doing but need to do (i.e. keeping servers up to date).
    • Nick mentions Todd recognized the need for people to be interested and engaged in their work, and Todd has iterated upon that methodology in terms of the way people engage with the company and its products.
      • If you’re listening to this episode and intend to become a leader but have not thought through the importance of people understanding the purpose in their work, think on it. It was extremely important for Todd to share the vision with employees.
      • “How is my role here having a larger purpose for this organization? And hopefully that gives me some personal satisfaction and sense of accomplishment.” – Nick Korte, on the importance of leaders helping employees to understand the purpose of their work
    • Todd says he came from a field where he was able to work on multiple projects on a monthly / semi-annual basis. This kept him excited about the job.
      • There were legacy systems to support, of course, but there were brand new systems.
      • “I understood that that job satisfaction of having something new to work on is fresh, challenging, you have to really think…I mean hard, hard problems to solve.” – Todd Cochrane
      • Todd gives the analogy of working with airplanes. Both power and space are constrained resources, and there is a give and take between them.
      • Translating this to running a company, there is server space as well as mind space. They would not want to do something that will be an extreme burden from a technical support perspective, for example.
    • AI (artificial intelligence) has Todd a little frightened, but the strategy for the company is to not be locked into a single language model (Claude, ChatGPT, Meta, etc.).
      • “We’re using the dumbest AI we’ll ever use today. It’s exciting at the same time, but it’s hard to pick a strategy that is not going to be obsolete in 2 weeks.” – Todd Cochrane
    • Todd says right now (at the time of this recording), the economy is tight with podcasting being fairly flat. But he and his team have been through cycles of economic downturn and know what to expect, having been profitable every year of their existence.
      • “As long as you keep the green line above the red line I think that’s the key in almost any business industry. Otherwise you don’t survive.” – Todd Cochrane

17:29 – Developing a Useful AI Strategy

  • John understands the desire to stay flexible and diverse in terms of different language models and asks Todd about his AI strategy and where he feels like it will help podcasters.

    • Todd always likes to ask himself whether something the company is doing will help the customer base by saving time or making a customer product better.
    • Todd says helpful areas for AI use will likely be content creation and post production. Many companies are doing things related to social media, and Todd doesn’t think he wants to compete in that space.
    • The number one question Todd gets asked consistently by content creators is “how do I grow my show?” Any use of AI tools would need to help in this area.
    • The team at Blubrry has taken several months to think through a strategy.
      • For those who follow Todd’s shows Geek News Central and New Media Show, he is public about the things in the AI space with which he has experimented.
      • The “thunking” is in creating documents (outlines, drafts, proposals, etc.) and will likely be done by the AI. The creative individual will still be needed, but some of the show prep (based on creative thinking) could be handled by AI, for example.
      • “On the other side of it, you have to be the subject matter expert of your topic, your content, so that when the production piece is done by the AI you can validate….You are going to be the person that is going to review the output.” – Todd Cochrane
      • We need to remember that the output from AI tools will not be perfect and won’t be for some time. Todd says the work of his team will be to educate creators on this fact.
      • Todd references a book on NATOPS with all the information needed (sort of like a bible for the airplane). There is a disclaimer on the book that it is not a substitute for common sense.
      • For example, if an AI provides poor topic suggestions, we need to not use them. Podcasters need to know that these are merely tools to help with content creation and production.
      • Blubrry will be working on tools to help podcasters grow their show, but it will be tricky. People need to understand the models / AI tools will lie.
      • Todd says for a show like ours where we are having a ranging discussion, AI has a hard time summarizing it. But for shows that are one point after another, AI does well there. Nerd Journey may not get as much value out of a transcript analysis as a news show covering a set number of topics.
      • Todd shares the results of some tests lately that were lower quality than what an intern at his company should produce.
    • Nick feels like this is just the tools and the SME (subject matter expert) changing a little.
      • Todd says we (as the SME) need to be able to check to see if output is too flowery, if the AI added something that wasn’t discussed in a show summary, etc. He feels the tools will get better over time (pretty quickly) but just are not there yet.
    • John mentions these tools help with the problem of starting with a blank page as well as with summarization. It’s easier to work from a draft than from nothing.
      • Todd says podcasters have often been lazy with show notes.
      • “You record for your audience. You write for Google.” – Todd Cochrane on podcast creation and show notes (advice for the podcaster)
      • As language models become more widespread searches will change, and we want our content to be easily findable. The metadata we feed into Google is becoming more important.
  • To follow up with Todd on this discussion…

    • E-mail Todd – todd@blubrry.com
    • Todd is also on LinkedIn and many other places. Search for his name to find him.
    • Check out the podcasts he’s a part of as well:
      • Todd likes to say listening to the New Media Show consistently could essentially get you a PhD in podcasting. Rob Greenlee is the co-host of this show with Todd, and he has worked for almost every major podcast company over time.
      • Geek News Central is Todd’s twice-weekly tech show that is a broad range of everything technology.
      • Podcast Insider is a Blubrry podcast hosted by Todd and 2 others at Blubrry to discuss strategies for podcasting.
  • Mentioned in the outro

    • Our hope for leaders listening is that they would try to keep the same mindset Todd has about providing employees the ability to do interesting work.
    • We hope everyone listening has the chance to do interesting and exciting work every day. You can take control here as it is not 100% up to our managers to provide opportunities for us to do interesting work.
      • We can ask for more opportunities (different projects, work on new technologies, etc.) much like Jason Langer shared in Episode 218.
      • If both we and our managers are thinking about this, perhaps we can meet in the middle to find the right level of challenge, promote employee engagement, and provide the most value to the company.
    • Part of keeping the work interesting for the employee base may be recognizing when it’s time to part ways with certain employees.
    • The last part of our conversation with Todd focusing on the strategy for artificial intelligence technologies is about far more than just AI.
      • The CEO of a products and services company like Blubrry needs to understand how using new technology could help the company do things better to drive revenue, margin, and customer value.
      • The technologist needs to understand how new technologies will out of necessity or helpfulness integrate into the work we do or change the way we do it.
      • To avoid being disrupted in a negative way maybe we need to utilize the innovation budget in our own careers to tinker with or learn about something new / something to which we have not been exposed.
      • Consider what colleagues and peers are learning about for their own growth. Maybe it’s going to a conference to learn from others or to learn about what interesting problems technology vendors are solving in the industry.
      • Nick is reminded of the technology hype cycle discussions we had with Duncan Sparrell in Episode 249.
    • Have you ever tried creating a roadmap for yourself?
      • It might be analogous to signing up for a training course and a certification test because you have dates and milestones. Even if we have one for ourselves, how often are we looking at it to validate it’s something we want to do / a direction we want to go?

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