From Management to Organizational Leadership - Making the Transition Successfully

Making the transition from Management activities to Leadership activities is a challenge we see many engineering managers struggle with as they climb the leadership ladder. Yet, despite the endless training resources for new and progressing managers, the softer sides of this journey are often poorly covered or not covered at all. This post is Part II of a series to address these critical softer skills that are foundational to growth and success at the executive level. The first post focused on optimizing stakeholder relationships and management at the executive level, while this post focuses on the increased need to focus on leadership.

Management skills continue to be critical at the executive level, but the techniques for managing at scale shift as the size of the team increases. In addition to scaling day to day management, the importance of leadership skills increases at the executive level as it becomes more necessary to achieve outcomes through the full team by inspiring and setting a compelling vision for the whole organization to understand and align to.

Unfortunately, leadership skills often do not come naturally or magically to most rising managers and can hinder or completely stall progress into the senior level executive ranks without the right training, mentoring and/or coaching. Leadership skills are often even more challenging for engineers than for other disciplines (e.g. Marketing, Business leaders, Product Management) as engineering seems to attract on average more introverted individuals.

Let’s start with a common conceptual framework for management in contrast with leadership and build from this foundation to the implications for leadership behaviors and activities in the executive ranks.

A very simple two-word contrast is management as a Pushing activity and leadership as a Pull.

Building on the concepts above, leadership can be more tactically be broken down into key steps as follows:

• Creating a compelling vision that ideally connects emotionally with the team and “pulls” or motivates them to do the right thing for the company (and for customers and society at large!)

• Creating a mission statement that codifies the vision and moves towards action and creates a mental roadmap towards the vision

• Defining concrete outcome based goals that the team can begin to plan around

• Creating principles for how the team will operate. Principles should cover high level guidance on the optimal approaches that the teams develop to reach their goals including the key aspects of people, process and technology/architecture.

• A last and extremely ‘squishy but critical’ dimension of leadership is creating a healthy culture for the organization. Culture is critical and is built over time and cannot be forced. That said, it is built successfully by living according to your values and organizational principles day by day and week by week. There is no substitute for consistency in your messaging as a senior leader that should reinforce the organization’s vision, mission, goals and principles at every opportunity.

The above cascade from the inspirational to the tactical go a long way to setting a strong, scaled, organizational foundation for effective leadership. However, in addition, there is the hard work and focus day-to-day that are needed to truly scale as a leader which we will subsequently discuss in the following categories:

• Expanding mindset and level of effort on thinking about, distributing and managing the activities of today and this week to additional focus on the path for success in the future.

• Moving from having the right individual contributors to the right leaders – and being able to understand the difference between what makes a leader/manager successful and what makes an individual contributor successful.

• Putting additional focus on growing organizations, in addition to growing individuals.

• Delegation and learning to parse a vision that moves teams into concrete action rather than creating detailed subordinate step by step tasks. This follows on from effectively developing and more importantly making the layers of the strategy to execution pyramid a reality that the organization understands and drives to outcomes based on, daily, weekly, quarterly progress....

Let’s discuss what each of the dimensions above looks like in the real world.

Distributing and managing the activities of today and this week to additional focus on the path towards success in the future

As an entry level manager (normally managing ~1-3 scrum teams with a typical title of Engineering Manager or Senior Engineering Manager), you may practice many of the bullets below at a small scale. As you rise to senior leadership and executive roles, it is CRITICAL to budget and spend adequate time and devote mind share to the activities below:

• Strategic planning with direct reports – this activity involves taking the company strategy and cross-engineering priorities and creating objectives at the organization level to achieve the desired outcomes.
• Most customer/business priorities will require collaboration with Product Management but should follow on with Engineering alignment on execution.
• Many companies use OKRs as a framework for creating a trackable and measurable plan that aligns to objectives at all levels
• Ideally there is a quarterly rhythm to review OKRs (or name your framework) and score and make adjustments where appropriate

• Connecting the company level strategy and objectives to the day-to-day work the team is executing against. The above exercise of driving from strategy to a plan that results in measurable outcomes is the foundation for connecting the teams’ daily work to meaningful customer and business success. That said, we commonly see team members frustrated that they have no idea how their work connects to the company’s strategy and top priorities according to the CEO/C-suite! Here are habits/behaviors to help address this gap:
• Create a roadmap(s) as ‘connective tissue’ that clearly maps the path from high level company strategies and objectives to the priorities of your teams.
• Regularly communicate the teams’ objectives and reiterate the connection to the company level strategy as well as to customer outcomes. This is further discussed as part of scaling your organizational leadership through ongoing communication, both formal and informal in a later section.
• And always remember.......

“Without credible communication, and a lot of it, the hearts and minds of others are never captured.”

-John P. Kotter

Moving from having the right individual contributors to the right leaders

Although it is critical to have a real pulse on the organization at all levels, it becomes increasingly more important to focus on hiring and growing the right leaders as the organization grows. Following are practical strategies to building a senior management team:

• Build and work your network! Effective interviewing for skills and behaviors is important, however, interviews and tests that leaders are put through have become extreme in many organizations, even without data that supports better outcomes for the additional ‘rigor’ or hoops (e.g. cognitive testing, behavioral testing etc.). Like so many systems, interviewing, especially at the senior levels, has taken on a life of its own. For this and many other reasons, finding candidates through trusted referrals and your own network is often both more efficient and more likely to result in success – defined by the new leader's results and tenure. Cultivating your network of close and ‘loose ties’ also supports an increased level of innovation and is just as relevant today as it was when Granovetter published his seminal research in 1973!

• Deliberately look for blind spots and gaps in your overall leadership team. These gaps can often be identified subjectively and supplemented by tests like Gallup’s Strengths based leadership. Here are some example considerations when striving for a balanced leadership team:
• Technical skills – while leaders in Engineering must have a base level technology competence, it is appropriate in most situations to have leaders that are more/less deeply technical than others.
• Planning and Execution skills – ideally the leadership team has members that have a ‘default planning and execution mindset.’ This obviously helps raise the bar across the team to fire on all execution cylinders.
• Process and Systems orientation – these capabilities often correlate with Planning and Execution skills - but not across the board. Leaders who are strong in this area have a high interest in making the team more efficient by improving how work gets done through process and tools and ideally based on data that the team monitors on an ongoing basis.
• Strategic vision – while technology leaders tend to be curious, they are not always adept at taking the time and mental effort to consider step function changes 1, 2 and 3-5 years out. Strategic vision helps push the team mentally, supports innovation and is inspirational.
• Influence and ‘woo’ - these dimensions of leadership involve cultivating connecting with - and having empathy for others, often outside of the leaders’ organization – as human nature naturally drifts towards an us vs them mindset or “my team does everything right, but all the other teams are messed up.” It follows that the ability to develop strong relationships results in the ability to more effectively influence others based on a foundation of ‘safety and trust’ in the relationship. Unfortunately, personal connection/empathy and influence skills are usually weaker in Engineering teams compared to other functions that on average attract more outgoing personality types (e.g. Marketing, Sales).
• Diversity in thought and background – this often comes from different cultural backgrounds (ethnic, geographic etc.) or gender diversity but there are certainly more types of diversity that can achieve this balance. Diversity in backgrounds leads to diversity in thoughts and ideas and is perhaps the strongest dimension of driving innovation.

It is not a coincidence that the above dimensions have a strong alignment to the four quadrants of the Strengths Based Leadership framework:

• Execution

• Strategic Thinking

• Relationship Building

• Influence

Achieving this balance helps to navigate within and outside the organization more successfully as it represents a balance of interpersonal, execution and strategic capabilities. Relationship building and Influence tend to go hand in hand and are often weaker in Engineering organizations relative to the rest of the company as Engineers are generally more data and ‘just the facts’ driven than other areas (e.g. Marketing, PR, Customer Service).

In summary, it is critical to understand the balance, diversity and gaps in your leadership team on an ongoing basis and strongly consider gaps when a role opens up to fill. This can be done both subjectively based on your day-to-day observations and 360 feedback for your leaders and a more objectively through useful frameworks previously outlined.

A last note on growing organizations relates to succession planning (SP). While some organizations are very good at managing succession on an ongoing basis, many only pay lip service to it or don’t do it at all. Following are important aspects of succession planning:

• SP should be conducted 1-2 times per year and when a significant organizational change or departure occurs

• SP should consider all leadership levels with a heavier emphasis on the more senior levels

• SP should include an estimation of when the leader would roughly be ready for the next level AND their gap/growth areas

• Most important is the SP conversation across a leadership team to discuss and debate readiness. This is often a BIG reality check as to how leaders are currently perceived across the organization.

• The gaps/growth areas should be incorporated into an actionable development plan for all leaders (e.g. lead XYZ project, coaching in certain areas etc.)

• SP should consider which roles would be filled by a transfer from another org or externally if a role was to open up in the short term, based on the readiness assessment step.

Putting additional focus on growing organizations, in addition to growing individuals

While focus shifts towards the leadership team and achieving outcomes through others at scale, compared to driving the work more directly with smaller teams, it is still critical to have a pulse on the team level capabilities, challenges at a detailed level. Achieving this balance of top down and bottoms up is challenging for any leader, it is naturally more of a challenge to leaders that are new to managing large teams.

Following are practical strategies to help understand what is ‘really going on’ across the team:

• Having regular skip level meetings – meeting with team members 1 on 1 regularly, ideally multiple meetings per month for larger teams, go a long way to understanding what is happening across the org in more detail. Of course, you must be aware that not all people will feel comfortable sharing too much with management. If you actually make adjustments and support change based on the teams’ input, don’t break confidentiality/trust, these discussions can really help build and support team morale and drive continuous improvement. They are also a great way to identify talent within the organization. Following are additional tips on managing skip level meetings:
• Make a point of scheduling when you are visiting any office location
• Set a goal for how many skip levels you would like to have per week, month and/or quarter, schedule them and make it a priority.
• On the flipside DO NOT cancel or deprioritize these meetings unless it’s a true emergency. Especially if you have the meeting(s) on calendar and then cancel them, it’s worse than having never scheduled them at all as it sends the message that they are not important and/or your time is more valuable than your teams’ time.
• COMMUNICATE! COMMUNICATE! COMMUNICATE! - through both formal and less formal communication channels.
• Formal Communication - All-hands and team level meetings are important especially for larger topics such as OKR’s, company strategy updates, etc. In most organizations these meetings happen quarterly but can be at any frequency that fits the teams’ needs and/or when important new information needs to be shared and understood across the team.
• Less formal communication - A simple example is setting up a slack channel for teams to ask/discuss/raise concerns with you and your leadership team. The informal format often makes people more comfortable sharing their detailed challenges and concerns. Following are tips to make it work:
• It’s important you are relatively responsive in this type of channel or it will die (and create cynicism obviously).
• Set it up so you try to rotate who answers questions where appropriate, to help develop your leadership team and manage the discussion load.
• Use topics to guide focus areas for improvement, deeper analysis, topics for upcoming larger team meetings etc.
• Use smart tooling to objectively analyze skills at the team and individual level. Most teams use various automated code quality tools. Many of these tools have a dimension of analyzing at the individual and team level. Here are thoughts on questions you can address and do’s and don’ts of using them to help understand detailed team performance:
• Code linting tools (e.g. SonarQube) are a good source of data to better understand:
• Overall productivity and rhythm – who is checking in code, how often, how much....
• Who is creating tech debt? Who is cleaning it up?
• Similarly - How does newly created code adhere to arch principles/coding standards?
• While this information can be used to coach at the manager/team level and at the individual level it is important to be VERY careful and thoughtful about how the data is discussed in coaching conversations:
• If the team thinks the data is being ‘used against them,’ as opposed to in a positive, supportive way, it will backfire
• If the data is used to drive top level metrics, the team will start to game the metrics (unfortunately this is always possible) and will also backfire.
• And it follows that it’s also important to coach the management team on how to use the data as well, to support the team in learning and improvement, rather than scare, demoralize or ‘punish’ them.
• These tools as well as subjective or strategic assessments can also help identify where gaps exist in skills/knowledge and subsequently analyze strategies to address gaps in the short, medium and long term such as:
• Engaging deeply skilled third-parties to work side by side with team members and including a measurable training plan
• More traditional training, online or otherwise
• On the job training through internal cross-training and assignments
• At the senior level it becomes increasingly important to spend time understanding future trends in order to ‘get ahead’ of future gaps. Part of this involves spending time doing your own personal learning and:
• Inspiring learning across the organization – tell your team what you are learning and why and highlights of what you have learned relative to the company, its products and the team
• Recognize teams and individuals who are spending time learning, through informal communication channels as well as through all hands meetings and the like.
• Relative to skills and cross-organization influence, as previously mentioned, deliberately cross-pollinating with teams outside your area is key. This also supports better cross-team dynamics through natural relationships that expand as people move around. Natural areas for cross-pollination assignments include both ‘specialty skill areas’ as well as different product areas, for example:
• Security Engineering
• Cross-engineering architecture functions
• Other parts of the actual product
• Platform engineering

• Practice “good” - versus “bad” delegation
• Good delegation makes it clear the WHAT (the outcome) and WHY of the objective but not HOW to achieve it. The team should have a reasonable level of autonomy in how they approach reaching the objective. Following are additional considerations:
• While the team should have autonomy, which also helps build morale through ownership and accountability, you are still accountable for the outcome. Therefore, to scale effectively, you need the opportunities to share feedback where appropriate, e.g. product demos, architectural review processes etc.
• A simple strategy to ensuring you don’t tell the the team how to reach their objective is to be deliberate and monitor yourself in discussions to make sure that you are asking questions rather than offering solutions immediately, e.g. “what other options did you consider? And why did you reject them? How will you measure progress incrementally?”
• Multipliers is a good resource for tools and approaches to help ensure you are supporting and guiding rather than dictating how to approach an outcome




A Last word....as highlighted in these last points on delegation – YOU are ALWAYS accountable for outcomes. Remember the simple adage “Give credit to the team for all victories and [you] take primary accountability for all failures.” This is perhaps the most important dimension of leadership at any level and is unfortunately not practiced by many. Or remember the flipside and don’t be the ‘kiss up/kick down leader’ EVER!


We regularly coach leaders to support their success at increasing scale. Call us and we can help!