Questions I’m Asking (and the Problems I’m Trying to Solve)

As I’m putting the pieces together (and they are coming together quickly!) there are a number of questions that I’m asking not only myself but also a ton of other people so that I can get objective feedback, advice, and perspective on what I should ultimately put together and build.

I got a great round of feedback via the initial announce post although the #1 response was “So… what exactly are you building…?” which makes sense since I was intentionally vague to begin with.

But, as you can imagine, I’ll be talking (and showing) more as I move forward. For starters, here are some of the questions that I’m asking:

A few scribbes via my moleskine.

A few scribbes via my moleskine.

What frustrates developers and engineers?

As an software developer myself there are 1,000+ things that have frustrated me over the years as I have built projects for smaller, medium, and large companies. This is both a good and bad thing, naturally.

It’s a bad (and sad) thing because that means that our lives aren’t getting much better / easier and it’s a good thing because this means there’s a huge opportunity to create exponential value for our line of work.

So, here are a few things that I’ve jotted down in my notebook as problems to solve and/or opportunities to explore more fully.

“As software developers we get frustrated when…”

  1. … we don’t know if I’m doing a “good” job.
  2. … we don’t know if the work that we’re doing is really making a difference.
  3. … the work that we do isn’t fully recognized by the team or by leadership.
  4. … the work that we do doesn’t directly impact the business (i.e make money).
  5. … it’s unclear if the work that I’m doing is advancing my career.
  6. … it’s unclear if the work that I’m doing is helping me get a new job.
  7. … it’s unclear if the work that I’m doing is helping me keep my current job.
  8. … managers and leadership makes technical decisions based on “hunches” and not real, actionable data.
  9. … I don’t feel as if I have the resources (e.g. learning, education, tooling, help, financial support, etc.) available to do my job well, especially from trusted sources.
  10. … I don’t feel as if I’m getting the right amount of feedback through peers, management, or community.
  11. … as soon as I adopt something, a newer (better, faster) tech comes along and I can’t keep up.
  12. .. it’s difficult to know technologies/solutions are being used within my organization. In many cases, there will be multiple solutions used to solve the same problem.

Again, these are just some things that I’ve captured in my notes as I’ve been tackling the problems and attempting to find solutions. Feel free to add additional thoughts in the comment section below!

What frustrates engineering / tech managers?

I’ve also had the pleasure and difficult task of leading software teams, for both startup companies and even the Fortune 500. My challenges and frustrations as a technical manager have been just as large as the ones that I’ve had as an individual contributor (just different, as you would expect).

“As software managers we get frustrated when…”

  1. … we are not sure who my “top performers” are (and why).
  2. … we are not sure how to coach, manage, and incentivize my team to do better work and how to do real, value-driven performance reviews with real data.
  3. … we are not sure how to provide the best resources available to educate and level-up our staff.
  4. … we are unsure of just how much technical debt is being accrued and the real state of technical affairs.
  5. … we are unsure of who (and how) to approach progression and promotions for individual staff members.
  6. … we are unsure of how to provide data-driven, constructive feedback on work and productivity over time.
  7. … we are unsure of how our staff is doing and if anyone is unhappy and looking for other jobs.
  8. … we are unable to create a compelling and realistic picture of what our team’s technical culture is for new and potential hires.
  9. … we are unable to clearly justify human capital hires and restructuring.
  10. … we are unable to communicate to senior leadership data-driven metrics around our technical teams, their work, and their success (and opportunities for improvement).
  11. … we find it nearly impossible to adequately identify, qualify, and evaluate potential hires via traditional means (and other existing online tools).
  12. … we are unable to pro-actively detect (easily and early) someone’s productivity levels and when their contribution(s) are on the decline.

Again, just a first pass, but, there are tons more that you could possibly share with me! Hit up the comment section!

What frustrates senior leadership?

Finally, my career has afforded me the opportunity to be a senior leader in larger companies and technical cofounders of startups. And, the farther one moves up the less information you typically have in order to make more important decisions. Oh, the irony.

“As part of the senior leader team we get frustrated when…”

  1. … we’re not sure why certain technical teams out-perform (or under-perform) others.
  2. … we’re not sure how to incentivize our managers and their teams to achieve better results.
  3. … our teams do not seem to understand their direct impact to the business.
  4. … it’s difficult to create executive-level dashboards around productivity, output, and pretty much every engineering-based metric.
  5. … we are unsure of our exact human capital spend and how to best justify new hires or possible restructuring.
  6. … we are not fully briefed or aware of our complete technology needs, assets, and/or liabilities.
  7. … we are not sure if we are fully compliant, security and software-wise.
  8. … we’re unable to communicate a cohesive and data-drive narrative about our technical teams, our progress (and our wins) to the rest of the organization.
  9. … we’re unable to express unique technical opportunities (or potential threats) to the leadership based on real data-driven market research and awareness as well as our own product development.
  10. … we’re unable to provide the right coaching and insight to our leadership colleagues based on what is really happening within and without our organization.
  11. … we’re unable to clearly define and outline ROI and am unable to accurately determine how to correlate spend with the people, the teams, the projects, and the technologies that we have in place.
  12. … we’re unable to create real accountability and true visibility for those outside of the technical organization, even (and especially) the technical parts of an organization are becoming even more mission-critical and fundamental to business success.

Again, just a first-pass, but, these are all things that I’ve been thinking about immensely.

Please give me your thoughts in the comments if you have other “frustrations” that you’ve encountered or would love to be solved!


Click me! Go for it!

Or, tweet @WhatisPinpoint with a question, frustration, or problem you’d like to be solved so that we can all build better software.

You can, of course, make up your own.