From Developer to CTO Part 12: Management of Self

1. Management of Self

Not everything can be about the company or your staff – you need to dedicate thought and time to managing yourself, too.  In the chaos of work, efforts to be mindful of ways to improve your own experience get pushed to dead last on your to-do list and it’s easy to become resentful.  Outside of your own needs to enjoy your work, be productive, and grow, understand that there are risks to your organisation for not placing importance on this, and so your organization needs you to take care of and advocate for yourself, too.

1.1. Create Time for Yourself

I’m going to add my take on the oft-recommended time management activity of blocking regular chunks of time your calendar, without reiterating the obvious basis of it.

No one else will do this for you, and if an endless string of meetings is making it hard to get your own work done and to effectively lead your organisation, it comes to you and you alone to change the way you operate.  Your senior leaders expect you to be good at this; if you’re not it would be fair for them to question if you’re requiring this of your managers too, and thus your ability to lead and sustain a productive organisation for the long haul.

As a senior leader, finding yourself in an endless string of meetings can be an indicator of shortcomings in your ability to manage your managers, or to manage upward.  As it relates to your own managers, being dragged into too many meetings by them can be a sign that your managers don’t feel empowered to make decisions or that they don’t have the information or guidance to make correct decisions consistent with your values.  Creating too many meetings of your own can be a sign that you don’t trust your managers to report correct and complete information to you, or that they don’t have the skills to manage their responsibilities.  In either event, it comes to you to consider the effectiveness of your management style and ability to set expectations and vision for your managers, the strength of your managers to implement within those visions, and thereafter if you have the right managers in those seats at all.  Simply, don’t expect to be able to create time for your own activities if any of these considerations are suffering.  These are symptoms and you need to look inward for the answers.

It hardly bears stating that a follow-on symptom of this situation is finding yourself doing all your busy work and creative solutioning late at night daily, when you should be spending time taking care of yourself.  It is easy to become resentful but never forget that this can also be an outcome of your own design (or lack of it).

All in all, this recommendation isn’t about just blindly blocking time off on your calendar hang the consequences – it is about the goal of managing and empowering your organisation better so that you can.  Don’t let this stop you from pulling the circuit breaker when you absolutely need some time to consider your position though - it isn’t worth it to anybody for you to continue to push through when you’re completely frazzled.

1.2. Don’t Ignore Your Gut

Time and time again I have kicked myself for making incorrect, purely cerebral decisions when my gut was screaming at me to take pause and to consider a problem from more angles or dimensions.  The slight pause my gut has tried to create would have afforded me the opportunity to engage other people to better qualify a decision, or to create, vet, and verify the completion of a checklist before rushing to pull the trigger on an action.  Hesitation isn’t always a bad thing as long as it doesn’t result in paralysis.

1.3. Don’t Be Too Risk-Averse

The message in the preceding section shouldn’t be taken to mean that you should take pause on every decision.  Especially in a growing organisation you won’t always have the firm metrics you’d like to have to back your decisions, as much as being a “data-driven decision maker” is a desirable trait of any leader.  Experience counts, and some kinds of directional decision shouldn’t have to be driven by metrics.  Be aware though, that what may be an intuitively obvious, self-evident decision to you won’t always be so to someone else that does not have your experience, so be prepared to explain your position from a grounded, non-defensive stance.  Trust in your intuition and conviction are properties of good leaders.

1.4. Set Boundaries with Respect to Your Own Time

Even though it’s generally expected that executives work more hours than the average employee, it’s wholly reasonable to expect to have the same quality of life you’d want for your own people.  This can mean having to set boundaries with your own leaders and depending on your relationship with them that can take some courage.  If you don’t advocate for yourself however, it will likely be that no-one else will.  Remember though that your leaders won’t expect to have a pushover for a subordinate, so setting some boundaries should be something they’re responsive to and respectful of.  In having this conversation it is important that they know you’ll step up into your own time when you need to (even somewhat routinely. Yet, as it relates to their ability to reach out to you on your own time, give them a channel they can use for urgent issues but set the expectation that you will not be monitoring email or company messaging channels late at night or weekends as a matter of routine, even if you happen to be working after hours.  Allowing distractions after hours is just bad form.

1.5. Document Directionally Important Decisions

Every tough directionally major decision creates need for mitigations in one form or another, and often creates long term consequences to which you gave earlier consideration that are easy to forget about when they finally materialize.  As a technology executive I’ve often been in the position of having to explain some time after such kinds of decision were made how we ended up where we were, because the decision and its mitigations were not documented in a formalised way or in a known location.  Executives – myself included – have a lot of decisions to make and those decisions, risk, and mitigations may not always committed to long-term memory.  Not making things easier is that oftentimes important decisions get buried in long email chains, and these can be difficult to find in a pinch when you need to make reference to them.

In order to manage this, introduce the concept of a “steering decision register”.  Create the register in a known location using a tool of your choosing, and ensure the following are items are included with each decision:

  • The decision itself
  • Narrative supporting the decision
  • Parties to the decision, and who ultimately made it
  • Impacts to projects, timelines, and roadmap
  • Risks and side effects created, and the timelines over which those risks may materialise
  • Proposed mitigations

If you see a situation approaching where the price you predicted you might one day have to pay is coming due, it is important to illuminate the impending situation as soon as early indicators present and reference the decision document.  This document will serve to remind leadership how you got to where you are and provide context and justifications for the mitigations you now need to execute on.

When things get difficult for other parts of the organisation who are struggling with difficult outcomes, you’ll be on the hot set and no matter how much good faith there was when a decision was made, over time these things can get forgotten and the mood can change.  When it comes to perception of your own performance and your contribution to the outcome, this register could prove important to you if your performance comes under question.  This is an unfortunate position in which to find yourself but it does happen, and you need documentation to support you so you can set the narrative.  Avoid using this to assign blame as that is highly likely to backfire but do so from the standpoint that you win as a team or fail as a team, and that it was a decision that you all made together.

1.6. Stay Humble

Few things are as off-putting as someone who feels they have to prove their worth by barging through meetings or the decision-making process, so don’t be that person.  If ego or your insecurities get in the way of the true spirit of collaboration, you’ll never garner the full respect of your people or your leaders.  Don’t be the person in the room has who has to be “right”; it’s more productive to be vulnerable and ask your team to offer up suggestions to help inform the best position on something.  Be constantly mindful of the way you’re coming across and read the room.  If you sense your people disengaging from you, take a step back and re-engage them by asking what they think.  Humility will go a long way.  If you have the mindfulness to recognise this pattern in yourself when it happens, and you are so inclined, try to get in touch with what is driving the insecurity that is setting this up.  Overcoming the reason for those will be one of the most game-changing things you ever do for your career and personal development.

2. Conclusion

Even if you implement none of my ideas, if anything I've written has introduced you to, or improved awareness of, some of the considerations that need to be understood to succeed as a technology executive, then I feel I've succeeded.

I've written this series from a truly open position including my failures, learning experiences, and successes, and I hope this has created a more personal connection to the content and given you a chance to ask yourself how you feel and think about these areas.

Thank you for reading - on to the next challenge!


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