1.1.1. Managers Who Were Engineers
1.2. Don’t Make a Habit of Being the “Idea Person”
1.3. Don’t Ask Them to Have All the Answers in a Pinch
1.4. Ensure They Can Recapitulate Your Vision and Values
1.5. Assess Their Ability to Handle Ambiguity
1.6. Personal Style and Fostering Culture
1.7. Go “Between Decks”
1.8. Coach Managers in Providing Tough Feedback
1.9. Promote Visibility
1.10. Meaningfully Reward Them to Retain Them
1. Managing Managers
Managing managers is a very different skill to managing coalface staff such as engineers, and it isn’t just about project management, resource management, and delegation. Your managers need to be able to align with your vision and value set and use that knowledge to guide their decision making in support of the activities of their own staff. Ultimately, managing managers effectively is about providing them the enablement and environment for them to solve your problems for you, and you not taking too heavy a hand in solving their problems for them. They are an extension of you.
This section isn’t about which tasks managers need to manage or how they do them; it’s about giving them the best chance to be great leaders by thinking “outside the task”.
1.1. Understand Your Managers’ Backgrounds
Understanding the career heritage of your managers is important to modulating the way in which you manage and enable them. I’ve generally seen that development managers fall into one of two broad categories; those with a scrum master and/or project management pedigree but without a development background (your CSM and PMP types), or those that do have a development background and may have anything from no formal education in a scrum or project management discipline to a high degree of the same.
1.1.1. Managers Who Were Engineers
Managing managers can be a challenge for someone who has come up through the engineering ranks for a couple of reasons. Firstly, management discipline isn’t generally an experience set that they’ve spent years honing like their technical skills. Secondly, engineers natively tend toward solutioning because it’s in their DNA, but as a manager this can actually get in the way of establishing successful managerial relationships and proper enablement of your managers and coal-face staff. They tend to solution rather than manage. A struggle for these types of individuals is that they can sometimes irritate senior leadership because they do not speak in abstract enough terms to which the business can, and that can make it hard for senior leadership to fully understand the risks they’re working with.
It’s not uncommon for this individual to get to this position by virtue of success as a senior engineer who proved they can make things happen, perhaps by way of effective coordination of the technical activities of a small number of teams, with a modicum of interaction with the product function. Some may even still be an active contributor to the code base. Yet the ability of this individual to roadmap, plan, manage upward, and to understand and lead people may be underdeveloped and cause problems. Nevertheless, for the right individual with the right goals who is introspective and open to coaching, they can be developed into a dual-skilled, potent manager who deeply understands the platform. There is a huge amount of value in this.
1.1.2. Managers Who Were Not Engineers
Before saying anything else in this section let me say this – I do not look down on non-technical managers at all. I’ve worked with some incredibly effective managers from scrum masters to product owners to program managers. Their success has largely been the result of a conscious focus on understanding of self, managing effective relationships, looking out for their staff, managing upward effectively, and best practice as it relates to project management discipline. Well supported, this type of individual naturally tends to garner respect of senior leadership more quickly because they natively speak in terms that the business relates to, and the lack of technical discussion means conversations don’t get cloudy.
Naturally, the dynamic and expectations of a non-technical manager need to be different, and they need to be supplemented with appropriately mature senior engineers to get the comfort in their gut that they’re seeing things as they really are, and thus that they can understand risks and make the right recommendations and decisions. However, this manager will struggle to represent the platform well if they don’t have this relationship, and may find themselves in a position where they cannot explain (or stop) timeline slippage because they don’t have a good internal compass on what’s really going on.
Whatever their background, understand that their technical or management strengths can change where risk lives to some extent, and it ultimately comes down to your own experience to ask the right questions, listen to your gut, and your ability to create the appropriate balance in staffing to stay properly informed and complete the picture.
1.2. Don’t Make a Habit of Being the “Idea Person”
I’ll state again that ultimately, managing managers is about enabling them to solve your problems for you, and not you taking too heavy a hand in solving their problems for them. Of course, it’s important to be creative in your overall approach to vision, leadership, and long-range planning, and at the end of the day you will ideate in ways no one else is qualified to, especially as the most senior technology executive. However, it should not be standard operating procedure for you to think too far south into problems that your managers should be able to creatively solve. For the purposes of this section I’m referring to project management, administrative activities, and of course activities designed to improve engineering process and the “ilities”, for example.
At the risk of the following paragraph sounding obvious, in setting the imperative, be very sure to explain what you feel current state is so they know what you think they’re starting with. Be as specific as possible in describing the destination state. Follow-up further with what assumptions they can safely work with, and what constraints they must consider in solutioning. Initially, avoid giving them any leg up with an implementation suggestion and see what they come up with under their own steam; it’s important to learn how creative your managers are. If they struggle, dribble a rubric of an idea past them and see if it’s enough for them to get it over the line. This is managing the “who” and the “what”, not the “how”.
If they’re still not getting there, you know what you’re dealing with, and naturally you have to get more directly involved in discussion to come to the answer. Of course, if you’ve got your own idea then give it to them, but importantly use it as a coaching opportunity and describe why your solution is the one. Discuss why it works within the assumptions and constraints. They don’t necessarily have to learn to think like you, but they do have to come to understand how you think.
1.3. Don’t Ask Them to Have All the Answers in a Pinch
Not everything goes well all the time in a customer-facing world, and expectations can change quickly. Bugs can arise, systems can suffer outages, customers can come up with difficult requests, and the company may change direction on something when it’s least convenient to you. In these moments you’ll likely be on the hot seat to answer questions on timelines or how you managed to get yourself into a pickle.
Any reasonable senior leader to whom you report knows that in the hunt for information to drive recommendations and decisions, in a larger organization you may not have the information on hand at the drop of a dime. The information needed for decision making may be spread around multiple people and the answer may not be knowable until some discussion has been had between you and your team. The same goes for your managers; don’t put the pressure on them to be able to answer everything at the drop of a dime. As an executive there’s a lot of pressure you need to absorb in order to keep the environment positive and workable for your managers, so don’t let too much of it roll downhill.
If you’re in a difficult situation and need information fast, give them confidence that fundamentally saying they don’t know is ok, however, they need a construct to get them beyond there. Help keep them off their back foot by encouraging them to take a different approach to saying they don’t know, by making it clear to them as a matter of routine your expectation is that they’ll find the who, the how, and the when, by leading their team to come up with the best options. Naturally this is the same way you need to confer with your senior leadership when you’re in the hot seat, too. Don’t ever get caught saying you don’t know without following that up with a plan for how you’re going to find out.
1.4. Ensure They Can Recapitulate Your Vision and Values
You can have the best vision statement and value set in the world, but if your managers don’t buy into and live by those, they will be meaningless. They will have little to no impact on your engineering capability or culture, and your department will be, in effect, rudderless as it relates to the nuances and higher order maturities characteristic of an advanced engineering organization.
It comes to you to be incredibly crisp with your messaging because if it is not clear you cannot blame your managers for those values not coming to life. If you are effective at this, you should be able to sense in them a passion and personal connection to your vision and values, but if they don’t you need to work out why because that will pervade their decision making and culture. It could be that you didn’t do a good job articulating them, that they are well meaning but struggling to haul it in, or that they’re just not emotionally engaged enough to care. Either way it goes, you need to make sure you’ve got the appropriately motivated people in these seats because your success in managing the softer aspects of software engineering depends on it.
Importantly, the rubber has to hit the road as it relates to these. Yours and their management decisions have to be aligned with them (there will sometimes be justifiable excursions as these are guiding principles, not rules) otherwise your staff will see that they sound nice but really don’t impact the way in which you truly operate. You must stand by them. If you’re looking for a place to start, make them read this essay series, and construct your own playbook using the parts of this that feel most relevant to you.
1.5. Assess Their Ability to Handle Ambiguity
As an executive you won’t always be given totally crisp requirements statements from your senior leadership and sometimes it may even be a sole statement of desired outcome and that’s it. It will come to you to work out exactly what is needed yourself, and to lead the team in the conception of a solution with maybe very few working assumptions and constraints. This is a main role of a manager – make abstract thoughts into more concrete thoughts, with ideas becoming successively more concrete the further south into your org chart the process goes. In order to do this, you need your managers to analyse, ask questions, creatively solution with a set of assumptions and constraints they may themselves have to create, and offer a solution proposal back to senior leadership framed within those.
Simply put, if your managers are not analytical and creative, you’ll find yourself having to come down a level in your job function to do this yourself, and other functions of own job will suffer. Worse, your managers may become accustomed to not thinking these through themselves or taking initiative, and now you’ve got a harder job to restore balance. These are attributes that you definitely want to try and get a sense of during the interview process, but it’s an uncomfortable fact that you might not know for sure for several months after a hire how it will really play out.
Best case, even with little baseline knowledge, a truly analytical and curious manager will ask progressively deeper questions and can get understanding of a problem set relatively quickly. These are the people you want because they can have relatively immediate impact, create their own vision, and take charge. Some others may only become effective once they’ve been there long enough to have enough baseline information to work with (i.e., they understand things contextually), and this is fair enough as long as it doesn’t take too long; you expect to have to ramp up new managers for a while.
It may ultimately prove clear that you don’t have the right person in their seat. Some people have a hard time visualizing a problem set, and therefore keeping their thoughts organized in its mire is a challenge. This is a hard problem to fix. It’s expensive to replace a person as quickly as a few months, but it gets more expensive the longer you let it go on. If this makes you feel bad remember also that if they don’t have the vision, their team is likely to end up misled because they don’t understand the imperatives driving the desired outcome. You’ll need to get involved, and this effectively flattens your organization. You cannot really afford to compromise for long here.
1.6. Personal Style and Fostering Culture
I’ll take a manager who has issues with ambiguity any day over a manager that does not understand people and who does not have the requisite emotional intelligence. If a manager does not know what it feels like to be part of a good team they likely cannot manage one, and the damage they can cause is tremendous. To be specific if not obvious, if a manager’s personal style includes any of the following traits you have a problem:
- Egotistical or arrogant
- Inflexible and pushy
- Hyper-competitive
- Too abrupt
- Doesn’t listen to their team
- Argumentative
- Tone deaf to the feel in the room
- Lack of introspection ability (not self-correcting)
- Must be right
- Bad at receiving or giving feedback
Now, it’s one thing for a manger who reports to you to be this way with you because you’re empowered to address the issue, but it’s quite another if they’re the same way with their own reports who won’t feel as empowered to raise concerns about their manager’s style. Your best intentions for great culture will go unfulfilled if you don’t actively observe and correct their performance in how they deal with their people. This is one of the main things you want to look out for in going between decks (see below in the section “Go Between Decks”). I’ve had to fire a manager before because of their team’s complaints about their manager’s personal style, resulting in them coming to me with “please help or else” type conversations. At the end of the day, the manager proved too resistant to feedback, and keeping culture was more important to me than that manager’s individual contributions, engineering prowess, and my timelines.
On the positive side, you want to actively recognize your manager for exhibiting these following traits:
- Humility
- Absence of ego
- Recognizes and encourages their own team members
- Is good at giving and receiving feedback
- Calmness under pressure
Make it clear to them ahead of time that you expect them to exhibit these traits, and when they do, tell them that you appreciate these things about them so they get reinforcement of their positive behaviours, perhaps after observing them in a large team meeting, for example. If they could do with improvement in any of these, include it in their personal improvement plan, get them to buy into the idea that it’s something they need and want, and don’t forget to reward them when they get there. A touch of vulnerability in how you learned these traits yourself will help.
I’ll further expand on this theme in a following section “Coach Managers in Providing Feedback”.
1.7. Go “Between Decks”
Inevitably, the culture you want to build and the messaging you want to promulgate don’t always make their way to the leaves of the org chart undiluted. Your managers’ personalities are always going to modulate the feel of the department and they’re going to put their own spin on what they perceive. This is normal to an extent but if you have middle managers who aren’t completely in tune with you and the tone you’re trying to set, this will cause problems because if the engineers don’t sense the colour of your personal influence, they may not feel connected to mission and the way you want things to feel, no matter how much you believe you’re saying the right thing.
During my time in the Royal Australian Navy, I became accustomed to a tradition called “going ‘tween decks”. This is a practice whereby the Commanding Officer – without previous announcement – leaves their usual confines of the Bridge, Captain’s Cabin, or the Combat Information Centre and proceeds to wander the ship talking to crew members from all departments and at all ranks, and in particular, those in lower ranking roles. This is done because the Captain assumes that the abovementioned inevitability will manifest itself in some form, and by assuming he’s either not getting the whole unbiased story from his junior officers or that they are just not clued into what is happening on deck, he creates the opportunity to get a feel for the truth directly.
Even in the Navy, this is something that needs to be done with sensitivity, because department heads, junior officers, and senior sailors quickly become nervous if they feel like they may not be “buttoned up” in all respects. Additionally, the crew worry about reprisals from their immediate leadership and unless they have a real sense of loyalty and respect for the Captain, they might not give it to them straight-up. Captains need to be creative in how they get their information and subsequently handle changes and feedback based on their conclusions so as to protect the source.
Now of course being so brazen as to try this in the civilian world would establish a fear-driven culture and be completely counter to the goal you’re trying to achieve, which is simply – find out what’s really happening on the ground, and how are process and personalities influencing (or influenced by) those.
In your own department, establish “non-formalised” ways to keep your ear to the ground on a routine basis. Without undercutting your managers, find ways to keep yourself in conversation with people at all levels in your department with sufficient regularity that it becomes considered par for the course and doesn’t raise any alarms that might taint the information you’re getting. Never give direction to subordinates that aren’t your direct reports; use this simply as an information gathering exercise. If this information reveals weakness in process or personnel then it can be brought up as feedback and action taken through the regular “command chain”.
If this seems sneaky, understand that human nature almost guarantees issues at some level, and unless you have absolute trust in all levels of your management, it comes to you to take steps to ensure the culture you want is really playing out. Either way, establishing culture is your job, and this cannot be a passive process.
1.8. Coach Managers in Providing Tough Feedback
Earlier in my career, giving feedback with the goal of improving a manager’s performance was easily the most terrifying thing I had to do, short of outright separating someone from the organisation. Between my concerns about how the team member would take the feedback, and whether I would be able to deliver the feedback in a sensitive yet effective way, I always approached feedback sessions with trepidation. There was an underlying fear in me that by the time the conversation was complete, the experience could have proven contentious, and the working relationship tarnished. Stated another way – I had a fear I wasn’t going to manage this in a skilled way, and they wouldn’t like me by the end of it. I had to develop a go-to technique, and I had to find my voice. After some experience, for me it came down to three considerations.
Before you get yourself into a position in which you must give tough feedback, early on in your relationships with your staff you need to establish frequent positive feedback to set yourself up for success. When a manager does something positive, provide feedback that you like what you saw, and do it often. This sets the tone that they’re appreciated and that you’re observant of their performance. This will make it easier for them to receive tough feedback because they know you’re recognizing what they do well. I believe this to be an overall more effective strategy than using the “bathtub” technique of good feedback, tough feedback, and good feedback again. To me that’s just a mind game to make the experience easier on both of you and it doesn’t come across as genuine, because they know you’re only giving them positive feedback to soften the blow.
The next consideration is proper timing. Feedback must be given as soon as possible once a situation has become apparent, or an event has taken place. This is important because the scenario has to be clear in both your mind and theirs. Given too late, it can come as more of a surprise and just increase the chances that it will get them on the back foot. Differences in recall can turn the experience argumentative. Given straight away, the reality of the situation should not really be under debate, and it can be kept “real” and un-obfuscated.
It seems obvious to say, but the last aspect was to understand the person and tailor my approach to them, rather than having a single style that was all about me. My super-confident “operator” types have generally been easy because I could do a “drive-by” of sorts; set up a 2-minute call, quickly state the observation, don’t hang around on the call long enough to belabour it, ask them to think about it and tell them to come back to me with their ideas, and then leave. They’ve generally not been the kind to take it to heart and required little handholding but saw it for what it was and then worked with me to change it.
It's not as easy with the types who take things more personally. It’s easy to say be respectful and empathetic, but that doesn’t do much to help you hit the mark when you’re putting someone on the spot. People often experience an underlying sense of injustice because they don’t feel their hard work is understood or appreciated (false narrative or otherwise) and this can drive some uncomfortable outcomes. The technique I have used in this case is to ask questions to get a sense of how they’re doing from a more personal perspective to set a genuine, caring tone, such as: “do you feel you’re working reasonable hours?”, “is your manager supporting you well?”, and “are you getting the help you want towards your goals?”. Follow up with a statement to the effect that you’re here for them so they should feel free to reach out if they feel they’re not getting what they need to succeed. Establish a tone of “you belong here and you matter to me”.
Having done so, establish a conversation; specifically, ask them to talk about how they feel they’re doing as it relates to the area that you want to discuss. Don’t be too direct and just come at them with your feedback. As they answer with how they think they’re doing or thinking (or did or thought) drive the conversation toward asking if there is anything they see potential to improve about it. Drive the conversation but let them do the talking – they’ll feel less threatened, and may even come up with the answer by themselves. To the extent possible, take a non-imperative approach with “I’ve seen great results in the past when…”, or “you might get better results if you…”, versus the more direct, imperative, and awkward “I need to you…”. This may all seem like trite advice but it can be a difference maker to how they remember the experience and how they feel about you and their job when they get back to their desk.
Critically, make sure your managers handle their reports the same way. This is one area in which you can sour an employee instantly no matter what culture you’re trying to create. It is important that you get a sense of the styles of each of your managers as it relates to this skill because the costs of being insensitive to their team are too high. This isn’t easy but this is an area in which you’ll thank yourself later for coaching them.
At the end of the day be comfortable in the knowledge that what you’re doing is the right thing and it will contribute to a better outcome for everyone, and don’t concern yourself as to whether they’re going to like you after the fact or not. If despite best efforts the relationship sours and they prove unreceptive to feedback you need to consider whether they’re a cultural fit. The chances are that if they’re unreceptive to feedback they might have a stubbornness that makes them problematic in collaboration which can drive friction in a team, and you might be better off without them anyway.
1.9. Promote Visibility
Trust is easy to lose if a manager conceals issues, whether it’s due to a deliberate aim of misleading leadership that things are better than they really are, or just not being experienced enough to realize the damage it can cause and risk it creates. Encourage your managers to be transparent with you and acknowledge a manager for coming to you with something that is going wrong, and don’t be punitive. The same goes for you with your own bosses, too. It helps your bosses understand and manage risk, and if they can they’ll give you extra support where they see you need it or ask for it.
1.10. Meaningfully Reward Them to Retain Them
You’ve spent all lot of effort crafting a match fit manager, so don’t let them go unrewarded when they’re working hard or being very successful; a good manager is not a commodity individual, and replacing one is expensive, difficult, and time consuming, and you’ll personally bear the extra burden if they leave. Drop them a grand or two every now and then to let them know they’re appreciated or meet a delivery milestone or coaching goal. This is especially meaningful when the demands on them are higher than normal for too long. Placement fees at 20% add up to a lot of money for a $150,000 individual, so don’t be stingy for the sake of a few grand every now and then. Budget for this so you don’t have to go back to the well.
Give thought to not telecasting that a bonus is a possibility attached to a goal. This is not a hard and fast rule of course, but the impact a surprise bonus can give is much greater and helps you avoid some potential issues. It is highly likely that they will be disappointed for missing out on a bonus for not meeting a goal, and worse, a situation could develop in which they insist they met a goal but by your own estimation they did not. This will almost certainly drive resentment.
1.11. Create Focus with a “Theme of the Week”
The goals of a roadmap or longer-term plan can get lost in the daily battles of management and it can be helpful to give your managers a mental construct to keep them focused on a shorter-term timebox. This is especially important if there is a lot of parallel work going on and context switching is happening constantly. More than anything, the theme of the week gives them permission to not think about other activities. This is freeing.
Generally, if a manager and their team are doing something not aligned with the theme it needs to be a conversation because it may indicate a lack of focus in execution or lack of clarity in vision or the theme itself. This is a great topic during your regular meet-ups, an aim of which should be to verify the goals of the theme are being met.
The theme of the week concept also forces you as an executive to focus on what is truly important. If you cannot clearly specify a theme of the week that is achievable, you need to recalibrate your priorities.
Next Up
Generally there are more engineers than managers in a technology organisation, and the diversity in their skills and personalities can run the gamut. It is important to equip your managers with the skills and awareness to manage their engineers and this starts and ends with understanding them, so I'll continue my discussion there.
You can view my next post titled "Understanding and Assessing Engineers" here.
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