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Wise Words from a 20-Year IT Veteran on How to Work Better, Hire Better, and More


November 8, 2016

6 minute read

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What should you look for in a new IT hire? What can IT do to improve its relationship with HR? How do you gain credibility and win budget as an IT professional?

It’s questions like these that CIO Advisor, Director at ME8 Consulting, and 20-year IT veteran Gavin Whatrup answers on a daily basis. During his keynote session at Cloud IT Live, Gavin shared valuable and actionable insights about winning budget and gaining influence as an IT professional. But you can only cover so much in an hour.

We wanted to give our BetterIT Slack community members the chance to chat with Gavin in real time. The question and answers below are the results of our AMA with Gavin. The AMA covered topics like hiring, managing remote teams, navigating cloud challenges, gaining company-wide influence, and more.

Note: You can read the recap for our first AMA, which focused on security, here. Our AMAs take place in the BetterIT Slack community, which is a growing community of nearly 600 forward-thinking and innovative IT professionals. You can join today here.

Hiring the Right IT People

Q: When hiring IT people, what skill set did you look for? How did you know a good candidate from a bad one?

Gavin Whatrup: Definitely personality. You can teach tech skills, but it’s really difficult teaching attitude and understanding. Bad IT guys are those with little or no empathy or understanding for those on the other side of the keyboard.

Q: Is it better to hire skills, experience, or personality?

Gavin Whatrup: Experience if you can afford it, but personality is critical and has to accompany experience anyway.

Q: What’s your favorite interview question for when hiring for IT?

Gavin Whatrup: Why? (That’s my answer, by the way, not another question!)

Q: Do you recommend MCSA/MSCE Office 365 certification exams?

Gavin Whatrup: I do, but depends on your profile and the need to develop your team. Also how critical Office 365 is to your overall use of cloud services.

Gaining Credibility and Changing the Perception of IT

Q: What is, in your opinion, the best bang-for-buck for changing perception of a technology team to a service provider and thought partner rather than a cost center or maintenance shop?

Gavin Whatrup: Without a doubt, engaging in conversations, and providing services that solve problems or add value. It’s a bit of a cliche, but in the end, we’re all looking for help for us to do our jobs, and value creation is the biggest and best thing we can do.

Q: In your HR & IT article, you talk a lot about the strained relationship the two departments have. What can IT do to improve their relationship with HR as well as with other departments in the organization?

Gavin Whatrup: I think being proactive, providing solutions that solve problems they think are critical (as opposed to ones you think are), and being willing to listen to their concerns, rather than simply raising your eyebrows. The more empathetic you are, the more understanding HR will be to any issues you have. And together you’ll work out a mutual understanding based on real issues rather than assumed or begrudged ones.

Q: You mentioned in your Cloud IT Live presentation that “to win more budget, you need influence. To win more influence, you need credibility and presence. To win those, you need to engage at the people level.” Is there a systematic way to do this, and any real-life stories you can share where this approach worked?

Gavin Whatrup: The quickest way to gain credibility is to gain support from your executives. And it really helps if you have the support of your line manager. At my last company, I reported to the CFO, and she was the one that persuaded the board to create a quarterly slot for me to present an update. It wasn’t long–15 minutes–but opened so many doors to one-to-one conversations after that. Also, she encouraged each company MD in my group to create a similar slot in their board meetings. Also, finance meetings, dev meetings, which eventually led to doing presentations in external conferences. People speak to people.

One of the net effects of this was that in a climate of budget cuts, mine was left untouched.

Working with Remote Teams

Q: What is, in your opinion, the most vital tool or technique for effectively managing a remote team?

Gavin Whatrup: The best tools will depend on the purpose. For tricky comms, always the phone. For general updates or quick questions, Slack is good, although it has some security concerns, Skype for Business, or anything visual such as Hangouts.

Q: What is the number one challenge when it comes to managing teams across multiple offices (different countries, etc.)

Gavin Whatrup: Time differences. Just scheduling busy people during normal hours is hard, but in and out of those can be a real challenge.

Slack or Honey are good for sharing ideas and content, and the former for real-time collaboration. But the best way to connect people and increase understanding is through conversation.

Managing Cloud Challenges

Q: Do you think that there’s a good compromise to be found between cloud and local services/tools that businesses could realistically manage, or do you think that full migration to the cloud is the best way forward? (Example that springs to mind: continued attachment to Active Directory.)

Gavin Whatrup: If there’s any doubt, hybrid is the way forward. At least initially. You don’t have to do it one hit but gently migrate, unless you have a good reason for the “big bang” method.

AD or some other form of ID management is essential. If you can’t control it, you can’t manage it. AD is just one version, but it’s the one that most people know.

Q: Favorite cloud security tools and why?

Gavin Whatrup: I’m more familiar with Microsoft’s Office 365 suite, so their EMS suite and built-in monitoring tools are great value.

I should add that selecting the best iDaaS tool for you, such as Okta, Ping, OneLogin is an absolute must, even if you’re not using any of the major productivity suites.

This Versus That

Q: Given you are more familiar with Office 365, what are your thoughts on Office 365 vs. G Suite?

Gavin Whatrup: Office 365 has the advantage of being pre-entrenched, especially in larger organizations. Google is more flexible in use for smaller organizations and startups. G Suite’s also cheaper!

You can use both if your pockets are deep enough.

Q: Mac, Windows, or Linux?

Gavin Whatrup: From a cloud perspective, any and all. I’ve worked in environments with those plus Chrome OS. In a browser-based world, it’s almost irrelevant. In a hybrid environment, multiple desktop OSs is more difficult, especially in a mobile world, where data is locally stored and on the move. Encryption is the key here, and that’s difficult to centrally manage the more OSs are in your estate.

Questions of Utmost Importance

Q: Shepherd Neame or Samuel Smith ale?

Gavin Whatrup: Shepherd Neame out of loyalty to my local brand. And Spitfire is one of my faves.

Q: Are/were you a Top Gear fan?

Gavin Whatrup: Massive! And looking forward to it coming back on Amazon Prime. Almost worth the fee by itself!

Q: Favorite book, audiobook, or podcast?

Gavin Whatrup: Favorite audiobook? (Well, of a sort, as it was originally a radio series.) The Hitchhiker’s Guide to the Galaxy, considering it was written in the 70s, by Douglas Adams (RIP), many of the principles in it still apply today. Hilarious!

Q: If you can have dinner with 3 people dead or alive, who would they be and why?

Gavin Whatrup: Three people. Hmmm. Winston Churchill, Douglas Adams, Cleopatra. WC, because I’d want to understand if he was really as bad as people say he was. Douglas Adams as I think he was a genius in predicting things relevant to the IT space. And Cleo, as I’d want to know what it was like to deal with Caesar and bathe in asses’ milk.

Q: Is your company name ME8 in relation to postcode of office?

Gavin Whatrup: Correct, ME8 is the first part of my zip code (postcode in the UK).

Q: Pineapple on pizza: An abomination, or taste revelation?

Gavin Whatrup: Not on the top of my list. So I’d say abomination. I’m more of a meat feast kind of guy, with extra Jalapenos. And hold the garlic bread. There’s only so many carbs you can deal with at one sitting. Peroni beer, of course.

Join Us for Our Next BetterIT Slack AMA with Andy Schwab, Author of Ultralight IT: A Guide for Smaller Organizations

We’ll be hosting Andy Schwab, author of Ultralight IT: A Guide for Smaller Organizations, for an AMA in our BetterIT Slack community. The AMA will start at 2:00pm EST on Friday, November 18.

Andy is an expert when it comes to running a simple and secure IT environment on a limited budget. Like many IT professionals, Andy was faced with an uphill battle when he joined Adventures in Missions, an organization with 250 employees operating in 50 countries around the world.

Andy created an ultralight yet sophisticated IT approach to enable his employees to work with technology, not against it. To learn more about Andy’s remarkable journey, you can watch his Cloud IT Live presentation in full below.