Ask Me Anything Highlights: Derek Wise




Derek Wise (CTO at Grapeshot & VP Technology at Oracle Data Cloud) joined us in Venturi’s Voice Slack on August 17 to host an ‘Ask Me Anything’.


Questions for Derek covered a wide range of topics – morning routines, building successful tech teams, predicted trends in ML/AI, favourite tools & apps, best career advice, and online gaming.


Below are some of the highlights from the event.


To access the full AMA Transcript and take part in upcoming AMAs,  join Venturi’s Voice Slack.



Question from @Tres


What impact has the Oracle acquisition had on Grapeshot?


I’m happy to report “good things”.  Just as individuals grow, so do groups of people and it’s no different for companies.  I wasn’t lucky enough to be with Grapeshot in the early days where five people were working in a small office on Kings Parade in Cambridge. But I can tell you it’s wonderful to witness the continual growth of those people who are still here years later.

We are learning all kinds of new things (this is my first Fortune 500 company) and also taking some of our ideas into the new organisation as well.  We’re putting our own stamp on lots of things too.



Question from @Matthew Bellringer


Have you got any tips for making people feel safe to take on a leadership role? Particularly in respect to organisations which want to move away from being so hierarchical and formal.


Matt, great question and yes I’ve got a few.


  1. Talk about your failures.  The perfect leader who has never failed is really hard to believe when they ask their teams to embrace failure.  Somehow we’ve been tricked into believing that leaders need wear suits and be distant and perfect to be good leaders.  Instead, what we want from our leaders is connection and honesty. I do at least.


  1. Make your process for failure a something your practice.  Part of the reason we do company wide demos is not just to show off the success of our teams each sprint but also to show we don’t always succeed and how we learn/adapt from those failures.


  1. Embrace the fact that your role as a leader / manager is more about supporting others than whatever you did before.  The more senior you are the more your role morphs into people support.


There are loads of examples of flat organisations out there and some with more success than others.  As a gamer I sometimes look at Valve and wonder what it would be like there. I’m not quite ready to see nearly pure anarchy in business structures but it is fun to imagine.



Question from @Squashie


Are there any commonly held beliefs about building successful tech teams that you feel are just plain wrong?


Yes, the biggest one is that “super-stars” make great teams.  I’ve seen attempts to build a great team by sticking the best programers in a group and it almost always fails.  Mixed skills, perspectives, and respect make great teams.

I love this article and the underlying research from Google if you would like a bit of light reading.



Question from @BDoherty


What should tech leaders be doing to prepare for AI-centric business ecosystems?


Learn to speak the language.  You don’t have to be an expert building systems in Tensor to know what it is.  I would focus on the high level concepts so you can help influence good connections between the work and the outcomes you are leading the organisation to.

An example I use quite a bit is is NLP with significant semantic analysis vs a probabilistic approach to context analysis in text.  I am by no means and expert in either area but I do know where the pros/cons are for each approach and can provide advice in areas that needs low latency and low fidelity that probabilistic is a better starting point than semantic in that situation.

As a leader you really shouldn’t get to far into solving the problem for your teams but focus more on making sure you can guide/support/challenge them to success.



Question from @Holly


What’s the best career advice you’ve ever received?


Holly, Great question and so many to choose from!  I think my very favourite was from a coaching group I was in back in 2007.  I joined a group call TEC that was basically a support group for CEO’s. I was struggling with getting what I thought was low performing staff.  I couldn’t get my head around why they weren’t giving it as much as I would.

The advice was:“Stop trying to make everyone like you.  It would be boring, limited, and the least productive way of working.”

I still get frustrated today when I meet someone with potential I think could work at another level but I try to remember that we need the diversity not only in gender, ethnicity, etc but also in how people like to work.  Not everyone is motivated by the same things.



Question from @Adam Ferguson


If you had the opportunity to start your career in IT again from the very beginning – what area of IT (JS, AI, etc) would you pursue and why?


I love this question!  I often imagine going back and expanding my skills in prue programming at the systems level.  I was never much more than a hack as a developer myself. I do wish I had spent more time closer to the code as it’s a tool I wish I had now and again. That being said, I have no regrets.  I made a choice to go more towards the management side because I found the rewards on seeing other succeed with my help being far more powerful to me than if I’d built it myself.



Question from @Ciara


What advice would you give aspiring Software Developer’s in the startup community? Operating from a “wearing many hats” stand point, do you run the risk of being a jack of all trades & a master of none?


I’d say you need to figure out what’s right for you, your role, and your future.

Specialists/Experts typically have more narrow uses and require bigger teams/companies to support them. Generalist come in very valuable in startups unless the need is very very specific. If you asked me who to hire in my own startup I’d be asking for a generalist who could hire specialists when we were ready to expand.  But, in a larger enterprise I would be looking for experts! Context and situation matters more in this case.



Question from @GeeBright32


Do you use coding tests as part of your interview process? If so, which and why?


Yes, I love a “reasonable” coding test.  I don’t care if it’s in person, online, with tech or not.  It’s a very powerful tool to understand an aspect of the person. Now, I do not like big giant tests that seem to be geared to prevent finding talent that could be just weak in a few areas.

Basic assessment tool, yes.  Used as a replacement for getting to know candidates, no.



Question from @BDoherty


What trends do you expect to see in the AI/ML space in 2019?


I am “hoping” to see more creative solutions to data annotation and curation.  A few years ago it was all about the algorithms, then the number of layers, but the root of the problems I see are with getting large enough data to build training and test sets.  I’ve worked with a few good ones but it still feels like the quality quotient is missing. I can get crowd sourced reviews on “is that a cat or is that a dog” but anything subjective or fussy the noise from crowdsourced seems to damage the training set so badly that we end us spending months building more expensive sets of training data with dedicated resources.  Then I have quality but the scale is limited. We need something new to really boost AI/ML to the next level.



Question from @Sam Davis


What tech startups have caught your attention recently and why?


I’m super interested in a number of ICO platforms.  Blockchain has some interesting applications but I’m hoping to see the promise of an electronic currency happen.  For that to work we need some drastic changes in tools and security. I’m keeping my eye out for those.



Question from @JamesDeeney


Do you have a fixed morning routine?


Kind of would be my best answer.  I love the books about breaking down your day into 5 min activities and such but have yet to find it right for me and my personal style.  That being said I do a few things regularly.

Slack / Email catchup:  I look for mentions and emails that need to be addressed in a hurry.  Everything else is sorted and flagged for later. I’m an inbox zero addict, I have my inbox empty as much as humanly possible.

-Gym:  I’m not a crazy fitness person but a routine of getting into the day with a quick run, some weights, and full breakfast is starting to become part of me.  For years I rolled out of bed with candy bar and coke in hand and headed to the keyboard. It takes a toll on “real life” and eventually you pay a high price for that behaviour.

-Get to work early:  I try to get in around 8AM before the mass of the dev teams (around 10AM) arrive.  I find it’s the time I can best get the stuff on my to do list done. After that I spend most of my days helping others with problems or in some case causing more problems as is appropriate from time to time.


Beyond morning:


-Stop work time: (As mandated by my wife)  Typically by 8PM we ban Slack/Email in our house.  Watch some crappy TV (Thank God Love Island is done) and hang out with family.

-Sleep:  I’m a zealot about sleep… 8 hours is a must… perfect darkness helps… no electronics.  Basically I need sleep to work at my best.



Question from @Tommy G


What apps/software/tools can’t you live without?


If I split this out into two group (Work/Personal) it’s a bit easier to look at.







Question from @Danny McLaughlin


What do you think about the game Fortnite and can you floss?


I have a 14 year old son and we seem to communicate completely on Fortnite and Discord now.  Me being a gamer makes Fortnite something I have to try/play. I do like PubG as well… I have yet to decide what I like better.  I’d still rather boot up Starcraft and go Zerg some bases… but I’m old so I think that’s still cool.

No, I can’t floss, dance, wiggle to a beat etc.  The first night I met my wife we were in a dance club and she whispered in my ear “Can you even hear the music?”.  Yeah, I’m that bad at dancing.




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