Joaquin Lippincott

The 5 Core Elements of Technical Advising

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I recently had a conversation with someone who was looking for some advice on selecting a technical advisor for their team, and she had some great questions. As someone with a lot of experience in digital she was aware that things in the tech space have changed dramatically over the past decades (I've written before about the impact of Cloud) and the question is given the landscape of today, what does a good technical advisor look like?

In many ways, the answer today is similar to what it has been in the past, even though the technical skillset has shifted dramatically. I believe the best technical advisors always needs these five core elements:

  1. Ok with being wrong
  2. Great communication
  3. Good vendor management
  4. Empathy
  5. Up-to-date with latest technology

1. Ok with being wrong

The first most important attribute for any advisor, is for that person to be ok with being wrong. This doesn't mean they need to like being wrong (few people do), but being wrong means you've learned something, while being right means you've learned nothing. When looking for a technical advisor you clearly want someone who is going to be right a lot - that's the nature of good advice - but they need to be ready to be wrong, and welcome it as an inflection point for growth, however major or minor it might be. A great way to test for this in an interview is to ask for examples where the candidate has been wrong in the past. Anyone worth their salt as an advisor should be able to identify several key inflection points in their career where they were wrong and have the humility to be able to share the stories as a moment of personal growth.

2. Great communication

The second most important attribute, being great at communication, can seem a little non-intuitive to most people. Technical folks aren't exactly known for being compelling communicators, but when it comes to advice giving, it's critical. If someone has great ideas and insight, they are open to learning new things (see #1), but they can't communicate their ideas clearly, things will be dead in the water. Often times, communicating complex technical topics requires different approaches for different people: sometimes a picture, often a metaphor or anecdote - it all depends on the listener. When selecting an advisor look for people who are eager to share what they know, and have the tenacity and creativity to approach things from multiple perspectives until it's clearly understood by all.

3. Good vendor management

In tech it's impossible to be good at everything. Knowing the latest and greatest means that historical tech may be a blocker. Even technical masters run into edge case technology they know very little about. Rather than trying to solve it themselves a good technical advisor will know when it is time to call in the experts and also know enough to be able to vet the vendors properly. Imagine you are the manager of a large hotel, with all the functions required (legal, plumbing, electrical, pest control, etc). It would be impossible to A) do everything yourself or B) keep specialists on staff for every task. However, a good hotel manager should know how to manage vendors, what prices they will pay, how to hold them accountable - and create long lasting relationships with the best vendors. When vetting a technical advisor, ask them about some things they don't do well, what vendors they go to help with those services, and why.

4. Empathy

Another often under appreciated trait when it comes to selecting a technical advisor is empathy, but without empathy no technical person will actually be vested in solving other people's problems. It's important to not mistake empathy, the ability to understand and share the feelings of another, with being so emotionally invested that tough decisions can't be made. Often times the output of a technical implementation can result in a workforce reduction, but just as often in elimination of repetitive, soul-killing drudgery. When vetting a technical advisor, ask them about a time they used technology to make someone else's work better. A great advisor should very pleased about all the people they've helped over the years and it will be easy to see how much they care.

5. Up-to-date with latest technology

The final key attribute is generally the one most people try to lead with. Amongst all of the attributes it is actually the least important, and it is guaranteed to be a moving target, year after year. As of writing this article, I am firm believer that we are in the Cloud era. And as such, I would look for certifications in one or more of the following ecosystems:

All technology being planned for the future should be heavily vetted for portability to the Cloud due to the almost crazy increases in productivity and cost reduction this makes possible. Beyond this if you are dealing with legacy technology (as most people are) a significant amount experience with the legacy platform (Oracle, Drupal, SAP, etc) is highly desirable. When interviewing I would recommend asking about both which cloud technology and legacy technology features the candidate is most excited about. In both cases, the answers should be easy, but the passion should be evident when talking about the Cloud. If someone is too enamored with legacy technology they really won't be able to take you into the future.

Date posted: June 26, 2020

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About the Author

Joaquin Lippincott, CEO

Joaquin is a 20+ year technology veteran helping to lead businesses in the move to the Cloud. He frequently speaks on panels about the future of tech ranging from IoT and Machine Learning to the latest innovation in the entertainment industry.  He has helped to modernize software for industry leaders like Sony, Daimler, Intel, the Golden Globes, Siemens Wind Power, ABC, NBC, DC Comics, Warner Brothers & the Linux Foundation.

As the CEO and Founder of Metal Toad, an AWS Advanced Consulting Partner, his primary job is to "get the right people in the room".  This one responsibility is cross-functional and includes both external business development functions as well as internal delegation and leadership development.

A UCLA alumni, he also serves in the community as a Board Member for the Los Angeles Area Chamber of Commerce, the Beverly Hills Chamber of Commerce, and Stand for Children Oregon - a public education political advocacy group. As an outspoken advocate for entry-level job creation in tech he helped found the non-profit, P4TH, an organization dedicated to increasing the number of entry-level jobs in the tech industry, and is in the process of organizing an Advisory Board for the Bixel Exchange, a Los Angeles non-profit that provides almost 200 tech internships every year.


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