Welcome to episode 209 of the Nerd Journey Podcast [@NerdJourney]! We’re John White (@vJourneyman) and Nick Korte (@NetworkNerd_), two Pre-Sales Technical Engineers who are hoping to bring you the IT career advice that we wish we’d been given earlier in our careers. In today’s episode we share part 2 of a discussion with Anudeep Parhar, exploring the difference in the CIO and CTO roles, communicating with executives, conducting executive 1-1s, and progression from CIO to COO (Chief Operating Officer).

Original Recording Date: 01-06-2023

Anudeep Parhar is the Chief Operating Office for digital operations at Entrust. Entrust is a technology global company based in Minneapolis, Minnesota servicing two broad sectors – payments and identities sector and digital solution and cybersecurity sector. If you missed it, catch part 1 of our discussion with Anudeep in Episode 208.

Topics – A Moment of Ignition, The CTO and the CIO, Communicating with Executives, The Chief Operating Officer’s Lens, Passions and Knowing Yourself

2:37 – A Moment of Ignition

• Nick thinks it has to be hard to get used to walking into rooms with everyone in the room smarter than you. It’s not that you are not smart and do not bring experience to the discussion, but the people around you have a deeper, often different level of expertise than you.
  • This is not just book smart. People are a lot more savvy in their own disciplines.
  • You have to challenge yourself to walk into situations like this. If you want to be the smartest person in the room you’ve already lost.
  • Doing this is uncomfortable. It drives you to learn things you wouldn’t really think you need to learn. For example, maybe you realize you need to learn about what the FCC is doing about the broadband channel.
    • It may have little to do with your day job, but it definitely impacts you. This is part of a learning mindset that can be beneficial to us all.
• At Thompson Reuters in the 1990s, there was a lot of effort being put into developing people, including formal and informal mentoring programs. Anudeep feels lucky to have been there during this time and was able to meet a number of very business minded people (not just technology minded people).
• Anudeep very clearly remembers when his company originally acquired Thompson and the company creating a new entity. He was at the time a young engineer trying to figure out how to run a small team. The CTO of the company was picked to become the CEO of the company.
  • It was the first time a large company had made this kind of decision (the CTO to CEO promotion), and it was very empowering for Anudeep.
  • Anudeep learned that it is much easier for a technology leadership people to cross over into being business minded if you have the right attitude rather than a purely business minded person to understand the nuances of technology. It will be easier to upskill in business than if you need to upskill in technology.
  • Anudeep saw this and thought, "if he can do it then I can do it. What do I need to know to do that?"
  • "If you want to exist at those levels, you have to be in line of revenue. Figure out a way to get there. Fight hard. Be able to talk about how you’re in the line of revenue. Otherwise you’re just a productivity measurement" – Anudeep Parhar
  • At a certain level you cannot just be a cost and say that is what it takes. You have to be able to speak to how something enables and the business and therefore in line of sight of revenue.
• Anudeep was fortunate to work at a company with a lot of mentorship.
• He also believes you have to be out there in the community (for professional networking).
  • This was before LinkedIn, so you formed local networks with like-minded people and would push yourself to take the time for having conversations with others.
  • Platforms like LinkedIn have made this easier, but in Anudeep’s opinion, people still do not use it like they could be.
  • You have to put yourself out there and be humble about requesting assistance. Ask for 30 minutes, and make the effort to go see people where they are.
  • "You have to actively seek out mentors. Mentors are not going to come look for you. You have to take the initiative." – Anudeep Parhar
  • Nick mentions with a tool like LinkedIn, you have to determine how much time and effort you want to spend using it compared to other tools out there.
• When we see people who are more like us succeed at something we might want to do, it gives us more confidence that we can accomplish the same thing.

8:35 – The CTO and the CIO

• By CTO we mean Chief Technology Officer, and by CIO we mean Chief Information Officer.
• According to Anudeep, these roles are somewhat malleable with people in them doing different things depending on where you look.
• If you’ve been on an executive team long enough, there’s not a specific framework for the roles. They usually get assigned to make sure the team is cohesive.
  • Businesses have challenges, and you assign roles based on what you need done. It cannot be just randomly built but rather built on some industry definitions. Don’t take it too literally that there is only one definition of CIO or CTO.
• Since these are chief positions, you are the owner of whatever that function is.
  • Generally speaking CTOs are considered more outward looking technology if you have any.
  • Historically healthcare companies and other industries did not have / build outward looking technology and therefore only had CIOs (mainly concerned about internal technology).
  • A CTO’s stakeholders are generally customers, partners, and people who pay to buy your product / stuff.
  • If you’re a CIO your stakeholders are usually internal folks – colleagues, the board of directors, etc.
  • Numbers and money come into play here. We’re talking about the internal technology infrastructure (servers, etc.) and the budgets for it getting rolled under the CIO (whose budgets and span of control only grew by impacting internal functions).
    • This got rolled under the G&A (or General and Administrative Expenses) line on corporate income statements.
    • When that became big, there was a clear shift that happened. Unless you are a purely tech company whose primary focus is technology, CTOs used to work for CIOs because most it was part of the broader head of information technology and companies didn’t have much outward facing technology for a CTO to manage. This is one way it was structured.
    • Another way was if you’re a technology company your head of technology needs to be able to talk about the tech you built. There, the roles were reversed with internal IT reporting up to the CTO. The same thing happened with the Chief Security Officer as well (CISO).
    • Depending on the company, these functions could be collapsed into one organization, formed into a structured hierarchy, or could even be peer organizations. This is all evolving.
  • Generally CIOs largely look at internal technology and CTOs external technology. If you are a technology company, CTO is the head of all technology. And if not (healthcare, retail, etc.), a CIO usually holds the top job.
• How "technical" should the CIO be?
  • Anudeep says technical is a continuum.
  • Would you ever trust a company whose head of sales has never carried a bag (i.e. a quota)? The answer should be no. Would you ever trust a CFO (Chief Financial Officer) who has never done accounting work?
  • These are not generic general management jobs like they were 50 years ago. They are functional roles. Anudeep expects people who have the head technology job to be pretty technologically savvy. They don’t have to know how everything works, but if Anudeep said ChatGPT, a someone in a CIO role should at least know about it and not have to Google it right then.
  • Staying on top of current trends is really important for technical leaders whether they be CIO, CTO, or other.
  • When leading people organizations you need to be able to make reasonable arguments and justify why you think a certain way.
  • These are not general management jobs like general management jobs of old where you just preside over an organization. You are expected to know your stuff.
• For the would-be CIO…
  • For those who have worked in infrastructure organizations, there are businesses where all CIOs do is run networks and provision servers. That’s one way to achieve it.
  • Based on where Anudeep believes the industry is going, you need things like project management skills, the ability to run large cross-functional projects, and leadership skills to get there. And you have to be able to zigzag a little within functions.
  • Within traditional technology organizations, there are infrastructure people, project management people, application development people, and then application admin people (i.e. those who maintain large Oracle / SAP ERP systems).
  • In order to move ahead you have to be able to show that you can do more than just one piece. You do not need to be an expert in all of them, but you need to be able to say you have the wherewithal to do them.
  • Gain more skills. If you’re a core infrastructure person, try to get into the application environment. If you’re in the application environment, try to get into application development. And do it early in your career.
  • No one is going to look down on you for doing many different things over the course of several years. People actually like to see it. Anudeep personally went through this.
  • Anudeep’s first job (at Thompson Reuters) was 16 or 17 years. And he’s had 5 jobs since then. He’s felt bad taking roles for just a couple of years, but in hindsight, they were deliberate choices he made to gain other skills (which is how he explains it).
    • He wanted to get into healthcare, how to bring a company in house, how to build and sell a company, etc.
  • If you want a CIO gig or head of technology gig, try to get into at least 1-2 other functions, and don’t be afraid of only doing it for a year. That’s fine.
  • Things are seldom given to you. You have to take the risk and try it.

16:06 – Communicating with Executives

• You have to know the audience a little bit.
• Anudeep projects a very clear picture to his organization that he is very commercially minded. He has expertise in areas as we discussed (how to build and run things, etc.) and proven experience doing it.
  • Over the past 10 years or so Anudeep has been shifting his viewpoint to be more commercially minded.
  • If you’re an individual contributor in Anudeep’s organization, you will get a lot more attention and time with him if you bring that point of view (wanting to learn the commercial side, for example). If somoene wants to come talk to him about other things, he has interest but not that much interest.
  • People need to know how to communicate and what to communicate. With that you need to know your audience and prepare yourself to talk about things the right way.
  • Many times you don’t need to go and say all the smartest things. Anudeep has been very fortunate in his career to have senior executives take his calls and met with him.
  • When you speak to an executive, bring a point of view on a situation, and bring something to ask.
  • Anudeep clearly remembers when at Blue Cross one of his peers ran the government business, which was very profitable. Anudeep had no idea of the nuances of health insurance in the government sector.
    • Anudeep went and spoke to his peer about some technology topic, which he really liked. But then, Anudeep asked his peer about his business.
    • It builds a relationship where people actually want to talk to you. People like to talk about what they are good at and what they do. If you can create communication like that it is a very effective tool that will lead to repeat visits.
  • Nick says this speaks to what we encourage people to do in job interviews – bring questions. You can learn all kinds of things from people just by asking questions.
    • Anudeep reinforces the point that people love to talk about themselves. Use that to your benefit!
    • "People love to talk about what they have done and how good they are at what they have done, especially folks who are successful. Use that because there are nuggets of learning there. Bring something to the table, and don’t be afraid to ask for something." – Anudeep
    • Most executives Anudeep knows will respect this approach.
• Anudeep says for most interviews done at his current company, by the time someone reaches his desk, they have already been vetted. It’s largely a fit conversation at that point.
  • Anudeep shares the recent story of interviewing someone for 30 minutes for a pretty critical position. He told the candidate in the first 15 minutes he wanted to hear about why they were having the conversation (i.e. more about why the person wanted the job). But the second 15 minutes was to be for the candidate to allow that person to ask Anudeep whatever they wanted.
  • Anudeep says you see a distinct difference in people when the 15 minutes for questions happens. They start asking about the culture, how aspects of the business works, etc. This tells Anudeep the person is excited and interested to work at the company. For whose who say they don’t have any questions, he’s not no sure they should be added to the company.
  • People need to take the time to prepare for these conversations, and leverage the fact that people love talking about themselves.
  • Nick says this element of preparation is important. Don’t forget to use the tools available to research those you speak to in advance!

21:12 – The Chief Operating Officer’s Lens

• Anudeep says titles and compensation are very important. Don’t let anyone tell you they are not.
• In addition to this, Anudeep likes developing people. Over the years in the jobs he’s had Anudeep remembers a lot of the tech built, but largely he remembers the people. It’s the people he has developed who are now in better jobs and running large organizations (i.e. people who are now CIOs at large organizations). Anudeep says it’s fun to see this.
• One of the commitments Anudeep had made to his CEO and board of directors was developing someone inside the organization who had potential to fill his role as CIO in the event he decides to leave the company.
• Also, outside of technology operations, Anudeep could provide value to the organization as someone with a broader operational point of view.
  • Anudeep loves being out with customers as well as talking to partners and brainstorming to help solve problems.
  • Anudeep says two thirds of this was him wanting to provide an opportunity to some very smart people within his organization (like the now CIO of Entrust as well as the new CISO).
• That gives Anudeep time to focus on more of the commercial operations, and with the company’s growth he gets to sort of fly at a different altitude and impact more areas.
  • Managing managers is one thing. Managing VP level people is another. Managing C-level executives is a totally different thing. These people are high performing and high achieving. It’s a growth and stretch opportunity for Anudeep as well.
  • Anudeep brings reasonable humility to what he does. It’s not about him but about the smart people doing the work. Anudeep is fortunate to have management and a board who supports it.
• What kinds of things is Anudeep looking for in a 1-1 discussion at his lens?
  • Anudeep works with great people and wouldn’t send them a form to fill out beforehand or anything, but there are basic structures in use.
  • Even if the dialogue is more informal, you know the key points you need to hit and must make sure the people you are having a 1-1 with are clear on what the expectation is.
  • There’s a concept called the ten five. If it takes you ten minutes to explain it and five minutes for Anudeep to understand it, a 1-1 makes sense. But if it’s longer than that we should have a dedicated meeting on the topic (gives time to look at something and absorb).
  • A privilege of being in positional authority is the ability to clobber anyone’s calendar.
  • A 1-1 is really Anudeep being available for the said person (a subordinate, a peer, etc.).
    • And if the person does not show up, Anudeep will not be offended. It’s a time to have a conversation on what the other person wants to discuss.
  • If Anudeep needs something specific he will setup a meeting and send the person what he’s expecting in advance.
    • He believes in the importance of setting goals for a meeting very clearly (including the outcome you are looking for) and using the subject line for the meeting appropriately.
    • After the meeting you have to follow up with action items from the discussion. Anudeep likes to write it down and send it out so both he and the other person remember what was discussed and the action items.
  • You need some formalization on how you do 1-1s, how you do meetings, especially if you are running large organizations.
• If you impact growth and other organizations in the company, you need to be able to do quarterly business reviews (QBRs), discuss operations reviews, etc. Structure is important.
  • As you are part of larger organizations, not everyone may care or want to do a QBR, but you have to show line of sight.
  • There are corporate QBRs with the CEO to discuss how the business is doing and how to adjust (i.e. how revenue and margins are doing, how different business areas are doing, etc.).
  • Then you have to bring that back from a line of sight to the next level of leadership down and make it a little more relevant to them, for example:
    • People are going to get paid this year (a very personal one).
    • The priorities are shifting, so if you see the company make a change, don’t be surprised.
    • "It’s good to have a line of sight. Not everybody cares for it or wants it, but absence of it is clearly felt (if you do not have a line of sight)."
  • You don’t have to do a physical QBR, but you have to be able to send out some materials about company performance and where challenges are. It prepares people for shifting priorities and helps them understand the reasons behind the changes.
• The comment about QBRs and operational reviews are examples of a leader (like Anudeep) knowing the audience downward and how to communicate it to them, making sure people understand how what they do fits within the organization (i.e. understanding their purpose).
• It’s hard to do it according to Anudeep, but it is important. And you need to make the time for it as a leader.
• "If you do these things consistently, nobody is going to thank you for doing them, but they will certainly notice when it’s not done." – Anudeep Parhar

29:40 – Passions and Knowing Yourself

• How does a busy technology executive prevent burning out?

  • Some of this is about passion for what you do.
  • Anudeep’s family comes first, and he cherishes the time. Especially during COVID and over the holidays, his entire family is together. Flexibility of working from home helps.
  • Anudeep isn’t someone who can completely disconnect from work. It’s largely because he is interested in what he does and enjoys doing it.
  • He will carve the time out. If the family is going to spend time together during the day, at night he may read up on items of interest and finish work tasks.
  • Music and performing arts are a big part of Anudeep’s personal life (sort of his happy place). He might end up in the middle of the night watching a 1991 Frank Zappa concert in Prague, for example. And it’s good for him when he does things like this.
  • Anudeep says you have to know yourself. He knows what brings him peace and calm, and he has to find time for it (which sometimes may mean doing it in the middle of the night).
  • Technology has advanced in ways that can help when we have limited time. If you don’t have time to read a lot of books, there are a number of tools and podcasts where you can get snippets / summaries. It is good to keep yourself informed at a very quick pace.
    • Anudeep also recommends Masterclass. He had been using it for a while and got it for his family for Christmas. It was fun to do that together as a family (i.e. listening to Samuel L. Jackson talk about how to act).
    • "You have to find time to do these things. Do not give up your passions because otherwise it becomes work." – Anudeep Parhar
  • There are late nights and much coffee, but Anudeep still likes to do what he likes to do outside of work. And sometimes you have to carve out the time.
  • Nick says taking the time to do things you like gives you energy to go and do things you need to do.

• If you want to follow up with Anudeep, you can find him on LinkedIn or Twitter.

  • Anudeep loves talking to people and giving back by helping others learn, and if he has the time he would be happy to do so.

• Mentioned in the outro

  • Regarding regular 1-1s with your manger, check out
    • Episode 45 – Career Conversations with Your Manager
    • Episode 12 on Effective 1-1s with your maanger
  • Check out these episodes with other executive leaders on their progression stories.
    • Episode 71 – Journey to Executive Leadership with Brad Tompkins of VMUG
    • Episode 72 – Board and Executive Relationships with Brad Tompkins of VMUG
    • Episode 93 – Leadership and Supporting Employee Potential with Paul Green
    • Episode 94 – Career Progression, the CIO Role, and Growing Towards It with Paul Green
    • Episode 201 – Generate Depth On-Demand with Yvette Edwards (1/2)
    • Episode 202 – Having Some Career Zigzags with Yvette Edwards (2/2)

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