Monologue

This is a rather long post as it captures the 13 days of lessons learnt and tips I’ve been sharing on LinkedIn. Definitely interested to hear other’s experiences and thoughts, so do drop me a comment below, if you feel like it.

The content here is predominantly aimed at new managers and leaders as well as new managers of managers, but hopefully others can benefit too.

1. Feedback loops become slower and it takes longer to see the impact of your decisions and actions, which can create self-doubt and insecurity creep

• Ensure you have measurable definition of success in place for yourself and that you refer to it.
• Set clear goal and expectations for what you are focusing on and make sure that you have either reliable qualitative or quantitative way to measure progress and success
• Rock your own feedback and actively seek feedback and don’t wait until your performance review time. Be aware that due to the position of authority (depending on environmental/cultural factor as well), the quality and quantity of constructive feedback may decrease.
• Grow your introspective and reflective skills to self-troubleshoot and expand your mindset and perspectives.
• Ensure you have a supporting structure in place, such as a mentor and coach.

2. Context switching increases by factor of N in terms of volume, frequency and types, which can be disorienting and overwhelming

• Learn to identify what brain power and energy types you are using in different contexts and optimize your schedule around that. You may need to grow your self-awareness skills through mindfulness practice (e.g. meditation). Keep experimenting. You may find that meetings work best for you in the morning or maybe that focus time works best for you in the morning and so on.
• Allocate regular focus time for yourself - your brain has limits. Block it off in your diary and guard it like it’s a precious stone. Accept that you won’t always be able to hold on to all of it as things may crop up, but do your best. You may find that having a bit of quiet time at the start and end of each day will help you prep and digest.
• Do reset your calendar every now and then to defragment as things creep in.
• Companies tend to have a heartbeat and a level of predictability associated with - learn to identify that and use it to your advantage as to how you plan your day and weeks. In a start-up that would be adrenaline pumped heart with low predictability, but as the company gets larger there will be times where certain things happen and activity escalates (e.g. performance reviews, quarterly planning).
• Look for delegation, and thus sponsorship, opportunities at all times.
• Give your brain time to adapt - it’s awesome like this.

3. You may feel less part of a team, which will affect your sense of belonging and can leave you feeling lonelier than before

• Accept that the moment you step into a position of authority it changes the relationship dynamics. This is something a new manager will start facing, especially if they are doing the transition in the team where they have been an individual contributor before.
• A bigger step-change for this is becoming manager of managers, so be mindful as you do make that transition.
• Avoid isolating yourself - it will leave you feeling alone with your challenges and increase your stress levels. Instead look to connect with other peers in the company doing the same job and outside (e.g. join meetups and so on).
• Make sure you have someone to talk to with whom you feel safe to share with (mentor, coach)
• Deliberately invest in building better relationships at work
• Take care of yourself outside of work socially and community-wise. It can be easy for work to become the sole source of sense of belonging, which is not a healthy dynamic.

4. The volume of information that you have exposure to may increases dramatically in both depth and breadth, which will feel overwhelming at times

• Your brain will adjust over time and will learn how to filter it and what to capture. Perhaps you will experiment and pick up some tools/techniques in the process.
• Make conscious deliberate decisions about what information you need vs want and why. The temptation to over-consume information to ‘stay on top of things’ (sense of control) is dangerous, so be strategic about it as a means to be tactical about your limited time, energy and brain capacity.
• Every time you make a step change in leadership reset your expectations and re-review regularly your information needs. Give yourself time and space to figure it out over time.
• Avoid being overly reactive to new information and apply self-control over the urge to explore/act on it unless needed.
• Learn to let go and live in an imperfect world where you can only focus on what’s on N things at a time.
• Accept that you will start getting exposed to information that you may not understand fully, so sometimes focus less on the information itself, but the thought processes and approaches behind it. Use coaching and curious questioning. Build trust.
• Develop your people’s communication skills, so that information is presented at the right level of detail given the context its needed. Give peers feedback on such.
• Make sure to allocate time and space to give yourself a chance to process and reflect.
• Build a support structure for your self - peer community, coach, mentor. Learn how others are doing things.

5. The general level of uncertainty and ambiguity will rapidly increase which may leave your feeling anxious, scared and out of control

• For new engineering managers it can be a big challenge emotionally, because there is no replacement for the predictability and early validation possible in the software development cycle (write code -> validate it works -> ship it to production). There are also no quick fixes after something goes “live”.
• Accept that with every leadership step-change it will feel like uncertainty will increase - in part because it’s an entirely new role, but also because there will be more moving pieces and more people involved in the execution.
• Avoid succumbing to the need for control, which is a natural tendency of the anxiety that comes and accept that you will simply not ever be in control. Adding more process, diving deeper into details to assure yourself is common action, but is a good recipe for burnout and dissatisfaction on the other side of it.
• Avoid over-thinking and looking for perfection in decisions.
• Accept that thing will go wrong - it’s simply a matter of fact. The best learnings come from failure (do we even learn anything when we succeed?)
• Focus on iterating on your ability to set clear expectations, communicate constrains.
• Learn to build trust, to let go and to build the right framework for you to have a “good enough” confidence and comfort with things, without over-indexing on reactivity due to the emotional impact of uncertainty.
• When you feel out of control, take a deep breath and re-focus on what you are in control of and deliberately let go of what you can’t. Don’t bottle that tension and stress up.
• Try some mindfulness practice to build emotional resiliency in what may seem like high pressure situations.
• Get someone to talk to - a coach, a mentor, peers. The worst thing you can do for yourself is be overwhelmed alone.

6. The mistakes that you make will have more impact than before, which can increase the level of fear, anxiety and internal pressure to get things “right”

• Watch out for the fear of failure causing anxiety, vulnerability, and behaviour such as perfectionism, overthinking, etc. Improve your mindfulness skills to pick it up.
• Accept that you will make mistakes. It’s not a question of if, but more of a question of when. At the end of the day, we are all human and as such we are flawed in many ways, so mistakes are part of our nature.
• Accept that you will fail. It’s a question of when, not if. Failure is hard emotionally, but is the best source of learning. Do we even learn from success?
• Identify your tolerance for acceptable risk and play around with stretching it.
• Do accept and acknowledge all the uncomfortable feelings that come with this - it will help build your tolerance, thus emotional resilience to them.
• Sanity check your emotions with some introspective questions, such as “What is the worst that will happen?”
• Swich from “What if “ type of thinking to “How will I handle”, but try to avoid getting into overthinking spirals. As you will learn, with time, there is no “right decision” - you can simply optimize for what you know at the time, hope for the best and believe that you will be able to deal with the consequences.
• Avoid working in toxic company culture, where failure and mistake is a dirty word.
• Use data to evaluate options and decisions.
• Don’t let your ego (bruised or not) to get in the way of recognising mistakes and failure. Have you seen mistakes being swept under the carpet by leaders before? It’s important to be honest, transparent and exercise humility and vulnerability when it happens and focus on the learnings and moving forward. Be real.
• Build yourself a support structure around you (manager, mentor, peers)

7. Your sense of achievement and impact may take a hit, which can create dissatisfaction creep and can affect your confidence.

• This is very relevant for new engineering managers who are transitioning from doing to enabling/supporting/empowering/facilitating/etc. This is because up until this point the sense of achievement is likely based (and measured) on direct impact made through output (e.g. code), whereas now the impact be less indirect and there will be a sense of lack of be output “to show for it”.
• This can be an even harder transition, when a manager becomes a manager of managers and thus steps out of the team that is delivering the impact.
• It’s normal - it’s an adjustment of how you measure you worth and value-add as part of the role transition you are going through. It can take time as it’s a mindset shift and your brain will need time to rewire.
• Re-think and redefine what you see as “win” and “impact” for yourself. Train your brain to start notice even the smallest of wins. Be your own cheerleader.
• Avoid self-lowering thinking such as “I am not being useful or not adding value”. There might be times where indeed you are not adding value to your teams as they are self-sufficient, so be mindful and aware when to refocus your time between types of focus.
• Accept that feedback loops are longer and thus it may take time to see the impact of your actions, so aim to set yourself measurable goals and get regular feedback.
• Watch out for your need for creativity and keeping your creative self fulfilled too. This will affect different people at different intensity. Find something ‘yours’ and focus on it, when you have time. Alternatively look to rebalance outside of work.

8. Your sense of expertise will erode and morph over time, which can challenge your sense of competency and result imposter syndrome

• It’s important to acknowledge that - the sooner the better. Every time you make a step change in leadership you are going into a new role. And surprise, surprise the goal is not to be an expert in your past role any more, so watch out not to act like one.
• As you make step changes up the leadership ladder, some of your powers (e.g. ‘knowledge’) will diminish, but some others will grow (e.g. influencing). However, there may be a temporary period where you feel the disbalance and it may be frustrating until you hit the rebalancing sweet spot.
• Managing someone in a role that you were very recently (e..g managing a manager when you were a manager recently) can trigger all sorts of insecurities if you don’t focus on nurturing your growth mindset. For example you may feel inadequate because you suddenly realize the way you did something before was not very good when you compare yourself/your approach to someone you manage. But, actually that’s awesome - you have just learnt something new, but also identified someone that’s very good at something that you can lean on. It’s all about perspectives. Also in general comparing yourself with others is no good anyway, so avoid in general.
• Watch out for assuming that you should have a right answer and even an answer to questions that hit you by direct reports. You can’t possibly have all the answers and assuming this so will erode your confidence and competency perception, which in turn will fill you with guilt and voila - imposter syndrome. Build some coaching skills and find mentors for your direct reports for areas they need, where you can’t support them directly.
• Be humble and learn. Ego is the enemy here.
• If you care about this, a wonderful way to maintain some level of expertise is to learn from others and the output of others in the company and outside (e.g. system designs/RFC that are being produced by teams). Asking lots of questions in a curious way and being upfront what you want to get out of it (e.g. not interrogating/challenging) can be helpful too. Going to conferences and meetups is another way.

9. Having an increased scope of accountability can put more internal and external pressure, increasing your stress levels

• Your emotional resilience will build up over time, but it’s absolutely critical to take good care of yourself at all times and find ways to cope with stress, anxiety, etc.
• Focus on growing people internally and hiring so that you can delegate and grow other leaders, whilst sharing the load to create sustainability
• Focus on improving your expectation management, communication, time management, prioritization, delegation skills.
• There are various tools out there that can help you evaluate your accountabilities and responsibilities and evaluate where the priority of your energy-spent should be. Ask your peers, your manager for opinions as well, where is your time and energy best spent as you may end up making the wrong assumptions.
• Learn to say no constructively, when needed - it’s a skill.
• Find a mentor and a coach to support you

10. Supporting (and working with) an increased number of people (direct reports, skip-level reports, etc) will have a toll on you emotionally

• Your emotional resilience will build up over time naturally as you get exposed to more scenarios and situations, but it’s super duper mega important to take care of yourself meanwhile. Whilst it’s easy to say “take care of yourself”, it can be harder to achieve as leadership can put you in a new place in life and how to do that may be non-obvious.
• Coaching and mentoring skills can help you turn what would be situations ending up with emotional baggage to situations, which end up with no baggage and positive forward momentum.
• Build self-awareness (e.g. through mindfulness practice and skill building) skills to help you improve your Emotional Intelligence and help you regulate and manage your emotional state better.
• Build self-troubleshooting skills, such as introspection, reflective writing to help you train your brain and build a mindset of seeing things the same experience from different perspectives and angles.
• Be clear with yourself what your values are as this will help you identify and acknowledge internal (in yourself) and external (with others) emotional conflict and thus work with it.
• Get a coach and a mentor. Don’t shy away from working on a deeper level, if needed, with a psychologist/psychotherapy professional as well - working with other people can be a great way to retrigger any relational or other traumas, or simply old unresolved experiences from your past whether you are aware of it or not.

11. It can be hard to say no and/or disappoint people

• Hard truth of leadership is that you will not liked by everyone and your job is not to please everyone, so the sooner you get comfortable with that - the better.
• Avoid taking ownership ownership or responsibility for the emotional responses of people (e.g. disappointment, frustration, dissatisfaction) as this will lead to unnecessary sticky guilt and feeling bad about stuff (and associated fear of letting them down due to ownership taken). Do maintain a curious mindset and perhaps help them reframe and evaluate things for themselves from different perspectives.
• Try to reframe personalization thinking (“I am disappointing them”) to de-personalized (the situation, circumstance, decisions and outcomes thereof. And no - I am not suggesting you do that when you need to own up to a mistake you’ve made, which is often people that don’t own their mistakes do, which in turn leads to double the erosion of trust.
• Never leave space for assumptions (for both yourself and them) - be honest and direct, even if very uncomfortable. Learn to be uncomfortable, accept it and cherish it - it means you are growing emotionally.
• Don’t internalize organizational limitations (aka circumstantial/situational limitations), which are negatively impacting people, as a personal failure (e.g. redundancies, teams becoming anaemic due to attrition, etc). Identify what’s within your control and influence and what isn’t as you don’t want to get sticky feelings of powerlessness/disempowerment, which will unnecessarily affect your confidence.
• Consider that what on the surface may seem negative, can actually be very positive when looked from different angles. E.g. delivering uncomfortable constructive feedback that may affect the other person emotionally may be tough, but it will be helpful for their growth. Letting go someone from a team may be helpful for the team and for them to find a better fit place, etc. Not having someone promoted might save them from difficult times if they weren’t ready yet.
• Practice and even do some role play with someone if that helps. Saying no and delivering hard messages is a skill.

12. When people you manage leave, it can create self-doubt and insecurity

• Don’t overthink it and make assumptions and focus on the facts and what you know and what your data points are telling you (e.g. feedback).
• Remember that people are empowered to make a choice for what’s right for them and that’s a good thing.
• Focus on the positives - often people will leave, because they have had a chance to learn and grow and have decided to move on to the next thing and use what they have learnt. Or it could be because they have found a place that they will earn more money, get more challenge, and so on and that’s good for them. Most of the time someone leaving can be quite positive, even if it creates practical pains
• Focus on having a solid succession plan in place to reduce the practical pain of people leaving.

13. You will be swimming in new and unfamiliar territory a lot of the time and this can make you feel vulnerable

• Vulnerability, when acknowledged, can be very uncomfortable. Even acknowledging it can be hard as it may go against the brain’s self-preservation instincts. It may take building some mindfulness skills and reducing your emotional reactivity and increasing your tolerance to the feeling get there.
• Embrace the feelings that come with vulnerability and don’t try to run way as that will only result compensatory/defensive behaviours, which are probably the wrong thing to do (e.g. micromanaging, too much process, etc)
• Don’t jump too quickly into conclusions and actions - check-in on your motivations.
• Ego is the enemy as it aims to protect our vulnerable self and thus deny us the humble growth mindset.
• Vulnerability is powerful and not a weakness, as when your emotional tolerance to it is built up it can empower you in many different ways.

Earlier in the year I helped Josh Sanburn and his team put together a podcast series on building Second Life for the Wall Street Journal called “How To Build a Metaverse” which I’m now really enjoying. It’s great to hear all of the amazing stories about the origin …