🌳 Who do I delegate to? A CTO’s guide to developing leaders: TMW #302 by CTO Craft

Hello again!

One of the most common causes of burnout in early-career CTOs that we come across in our coaching and Circles is sheer overwhelm - the demands placed on us as engineering leaders often outpaces the personal resources we have available. This is very common where leaders aren't able to delegate properly. In today's piece we dig into building a team of leaders underneath you, so there are ways to reduce the load. If you're stuck managing too much right now, you'll want to read this.

This week, we're also announcing our next Bytes London event in advance of CTO Craft Con, which will be on Nov 10th on Charing Cross Road in Soho - there'll be the usual chance to network and share a drink and food with others from the CTO Craft Community and beyond, and a panel of experts talking about the importance and value of building a personal and professional network of peers. We'd love to see you there if you're in the area - details below!

On with the show - have a great weekend

Andy @ CTO Craft

Bytes London - Networks for Tech Leaders: Creating, Using and Nurturing Tickets, Thu 10 Nov 2022 at 18:00

In celebration of CTO Craft Con Winter 2022, happening 14th - 16th November, we’re hosting an in-person Bytes on 10th November at ARBORETUM, London. Join us for an informative evening with experts and networking.

Whether you’re part of the C-suite or you deal with C-suite members, building your network inside and outside of your own business is a fundamental part of your role as a senior technology leader.

Who do I delegate to? A CTO’s guide to developing leaders

Engineering has a relatively linear path to the top. While it’s common for developers to be promoted based on output alone, it doesn’t always make for the most capable leaders. Senior technology leaders and CTOs need to analyse technological options, align them with short and long-term commercial business objectives, and translate and communicate these recommendations to non-technical peers and stakeholders, among a myriad of other responsibilities. Technology managers also need to understand the technology at a detailed level – including the cost/benefit review of stability, reliability and scalability – to make solid judgments and move things forward.

While it may feel controversial to say, the truth is the best engineers don’t always make the best managers. Some people cannot (or do not want to) shoulder the responsibility that being a CTO takes (will versus skill). Others, who may not be the team’s best developer, possess latent leadership talent that has not been showcased either through lack of opportunity or lack of mentoring, but with the right program of support can go on to become great leaders.

So, how do you, as a leader, ensure that not only are the right people climbing the career ladder, also spot those that might not readily put themselves forward but could be stars in the making with the right support? Well, it’s all about environment, opportunity, support and learning/teaching.

Stage One – Find and nurture natural leaders

First, don’t assume someone possesses good management and leadership skills simply because they express an interest in treading that path. Second, ensure that they are aware that there are different types of managers and alternative routes – not all engineers need to become a CTO.

Instead, recognise the engineers that show potential and nurture them. Have they exhibited creativity? Do they go that extra mile? Are they willing to share knowledge and always take a problem-solving approach? If so, documenting their output quality and achievements will help. For example: your engineer ensures appropriate tests are done for code completion and documents them accurately or before they are about to make changes that touch common code, they notify the team. Both actions indicate someone might be ready for a step-up.

To test the waters, and help identify those who are willing to rise to the challenge and show their preparedness for a position of authority, consider the following:

• Delegate – Don’t simply question if someone can cope with more responsibility, give it to them. Offer more challenging work or additional duties bit-by-bit, but make it a dialogue and involve them in the conversation; either suggest they’re ready for more during or give them space to ask for it during 1:1s and see where they go with it.
• Create opportunities to learn and collaborate – Whether it’s with team members, colleagues in other technical and non-technical departments collaboration helps form bonds with colleagues, improves performance and increases productivity. External training including attending conferences, joining communities and obtaining further qualifications, also offers opportunities for your engineers to showcase their skills, learn from and skill-share with their peers and other leaders in the industry.
• Proffer experiences outside of their own code base – This will push your engineers’ comfort zone and technical ability, and show you how adaptable they are. When introducing them to a new system or framework, encourage your engineers to consider four elements:

1. Purpose: understand conceptually what the system or framework does;
2. Architecture: take a view on the overall architecture of the system/framework;
3. Components: learn how the constituent parts work together; and
4. Code: deep dive by debugging significant flows through the code base

• Showcase alternative management routes – If being a CTO isn’t right for them, demonstrate your understanding of their skills and ability by opening their mind to alternative leadership roles such as Engineering Manager, Tech Lead, or Engineering Director depending on the size of the team. Encourage your engineers to follow a path that best suits them – some may naturally be better at managing people whereas others will be better at hands-on roles, with no people management such as Principal Engineer, Chief Architect, or Staff Engineer.
• Don’t force it – Also recognise that some people don’t want to be leaders, even if you know they’d be brilliant at it, and that’s okay. Some engineers genuinely want to be left alone to code, sleep, eat, repeat. Progress looks different for everyone and their reasons for not wanting to advance to management positions are both varied and valid.

Stage two – Create the right environment and tailor development support

Where stage one acts as a make-shift filtering system, helping you identify the engineers that show promise, stage two allows you to focus additional attention and tailor support to ensure those that have shown promise, learn and hone the necessary skills to become effective leaders. To do this, it’s important to create not only the right environment for leadership development but also focus on the skills that are required of good leaders:

1. Empower your engineers – This is the difference between allowing your engineers to take ownership and giving them responsibility. Show and teach trust by delegating authority and decision-making; share information and ask for their input. Empowerment helps influence employee creativity and encourages citizenship behaviour (helping others) which is crucial.
2. Emphasise the importance of Emotional Intelligence (EQ) – Engineering focuses heavily on IQ and capability, but an effective leader needs the ability to understand, use, and manage their own emotions in positive ways to relieve stress, communicate effectively, empathise with others, overcome challenges and defuse conflict. Encourage them to listen, ask questions and understand others’ views during standups, retros and pairing task/team projects.
3. Prepare them to be adaptable – Good leaders need to be agile and possess the ability to implement long-term, sustainable change. Adaptability is about being able to see different sides and access new ways of thinking, enabling quicks shifts and experimentation as things like customer needs, markets fluctuate and technologies change. Having a flexible thought process also allows leaders to use varying strategies and mental frameworks to ensure the right, rather than the ‘usual’ solution is found to solve a problem or create a forward-thinking, disruptive service or product.
4. Help them understand what technological management truly means – As engineers, they won’t have been party to wider, often confidential business discussions. Their first foray into leadership will need them to manage (sometimes competing) expectations, three cross-functional directions (down, up and sideways), and peers with non-technical skills/understanding. They will also need to possess commercial awareness and a business mindset that allows them to build a technological strategy that feeds into the overall company objective more directly, in addition to managing the product or service.
5. Encourage servant-leadership – Leadership is not about status or glory – servant leaders share power and put the needs of others first. They focus on the growth, empowerment and wellbeing of their team, thereby helping them to develop and perform to the best of their abilities. An engineer ready and willing to take the reins needs to comprehend that they are becoming the creator, shaper, protector and motivator of their team(s).
6. Tell them to reduce their coding time – Some engineers might relish the opportunity to step away from the keyboard and take on a more holistic role, others will find it difficult to reduce their coding time and attempt to step-in and ‘fix’ things/speed up delivery by doing it themselves. This often stems from an inability to trust others and delegate, which needs nipping in the bud if the role doesn’t require it. Failing to do so early, will lead to taking on too much and is a slippery slope to burnout.

Stage three – Handing over the reins

The final stage covers the point immediately prior to the engineer assuming a leadership position and for a period of time afterwards. It will ensure that their development doesn’t halt prematurely and leave them flailing. Management, strategic and hiring decisions will now fall to the new leaders and without the firsthand knowledge and experience to deal with them, mistakes can be made. As such, the following actions are recommended to more or less guarantee safety to the other side:

1. Highlight the importance of active and continuous learning – Developing as a manager is an ongoing process and the opportunity to learn from others is always possible and should be taken. Encourage ongoing management-related reading, training and help them understand that they need a growth rather than fixed mindset to be a truly effective leader.
2. Encourage them to seek out peer mentorship – Connecting with external communities and networking helps new managers forge relationships that can be helpful throughout the lifetime of their leadership roles. First time CTOs and senior tech leaders face new challenges: some can be addressed through common sense and transferable skills; others can’t. Connecting with peers and seeking mentorship can ensure they have a safe space to talk about their failures, learn from others’ experience and ultimately understand what ‘good’ looks like.
3. Provide help and support in the early days – Understand that a first-time leader may need to lean on you more at the beginning and encourage this (within reason). Some people respond well to a baptism of fire and being dropped in the deep end, but it can also mean mistakes are made that could have been avoided that lead to loss of confidence either in their own ability or from their team. The ‘stabilisers’ can be kept on as long as they’re needed and as the one that nurtured them, you’ll be able to see when they’re ready to come off.
4. Emphasise communication, empathy and feedback – Once they become responsible for others’ development and commercial success, it’s time for the new leaders to take what they’ve been given and pay it forward. This starts with effective communication that includes radical candour – caring personally while challenging directly. Whether it’s feeding back during 1:1s, strategy planning or stakeholder meetings, great leaders are great communicators and this needs to be emphasised and encouraged.
5. Discuss managing and resolving conflict – Conflict is common in the workplace and if not resolved can be fatal. It impacts delivery, interpersonal relationships, staff turnover and even company reputation. New leaders mustn’t shy away from conflict in an attempt to keep the peace/not fall out of favour, so they should be encouraged to understand its root causes and the best models for resolution.
6. Teach stress coping mechanisms – Burnout is common in leaders, particularly within the tech industry. Everyone has their own threshold for dealing with personal and professional challenges, but the fast-paced nature of technology can exacerbate this. If an engineer is going to step into a leadership role and last in it they need to understand their triggers, access support and ask for help and find ways to mitigate the challenges they face to reduce stress and ensure burnout doesn’t happen to them or their team.

Developing engineers into great managers is a process that requires long-term investment. Time and effort injected at the beginning of someone’s management journey will not only be beneficial for them, when they reach the top, they are more likely to give back and invest in those they work with and/or manage. This will help foster a supportive mentality that impacts the wider world of technology leadership and hopefully changes the face of it for the better.

CTO Craft Bytes

Philosophy of Happiness, Fri 28 Oct 2022 at 12:30 BST

With James Conroy-Finn, former CTO at Listora, Drest, BCG Digital Ventures and more

High-performing teams are made up of highly capable individuals fortunate enough to have climbed a hierarchy of needs. From the physiological through to the cognitive and aesthetic, we will explore the idea that innovation and effective collaboration are predicated on the healthy pursuit of happiness.

Grab your tickets now!

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Have an amazing week!

Andy