3 Tips for Middle Managers in “Day 2” Organizations

with my team at MOE, who taught me so much about leading well – I’m still learning!

Everyone wants it to be “Day 1”
Jeff Bezos’s 2017 letter to Amazon Shareholders had some piercing insights about running a “Day 1” organization. He doesn’t exactly define Day 1, but the concept is clear when he describes a “Day 2” organization: “Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day 1.”

There are many gems on running an innovative organization, but I’ll highlight two:

  • First, a Day 1 organization never lets itself be owned by process. Processes exist to serve an outcome – following the process should never be the outcome. “The process is not the thing. It’s always worth asking, do we own the process or does the process own us? In a Day 2 company, you might find it’s the second.”
  • Second, a Day 1 organization masters the cycle of rapid decision-making, prototyping, failing and trying again. Jeff urges his people to take action based on 70% of information they would ideally have, and to be willing to disagree and commit (rather than disagree and grudgingly assent): it’s helpful to say, “Look, I know we disagree on this but will you gamble with me on it? Disagree and commit?” 

I recently shared a part of Jeff’s letter on Linkedin, and the responses suggested two things:

  • Many look upon tech companies like Amazon with envy, because their organizations seem so “Day 2” in comparison
  • Most (if not all) of us want our organizations to be “Day 1”

What if my organization is already Day 2?

What do I do if my organization is already Day 2? This question is important to the area of “tech and public good”, the subject of my blog (www.techandpublicgood.com).

Why? Because the main reason organizations (Governments, civil society and private sector alike) fail to harness technology – or for that matter any type of innovative practice – that will clearly improve their customer experience and operations is internal resistance. In other words, it is because they are in “Day 2”.

It is often not deliberate resistance. It is a slow, painful death, precipitated by adherence to process and status-quo practices, and a lack of clear ownership for the outcome.

When it comes to building innovative organizations, “it’s about the people, it’s really not about technology” – I can’t agree more with Greg Godbout, co-founder of 18F, who said this in a recent Harvard Business School interview.

People matter, and in my experience, the level of innovation in an organization depends on the behaviours of middle managers. Middle managers are some of the most powerful influencers in an organization – they set the tone for their teams’ culture, and can almost singlehandedly dampen or stimulate innovative behaviour among a large majority of your workforce.

Forces that make middle managers susceptible to “Day 2” behaviours

Unfortunately, I have noticed that when people transition from “team member” to “middle manager”, gravity seems to pull them towards being “upholders” rather than “innovators”.

This could be the result of coping mechanisms to deal with increased responsibility. When promoted from member to manager, one takes on a multitude of new objectives. In addition to the original objective they were hired to achieve, they have to help their team navigate relationships with other departments, obtain resources and gain the confidence of their bosses, manage HR issues, and prioritize their team’s bandwidth. Email load triples; more time is spent managing upwards, downwards and sideways; the appetite or bandwidth for innovations gets lost.

I worked in 5 teams as a member and middle manager over the years, and have seen the following traps among leaders:

  • Falling into a “process-orientation” in their leadership style to cope with volume. Simply ensuring that process is being followed can give some comfort that the team is on the right track, without having to commit too much mental bandwidth. There’s limited upside, but also limited downside.
  • Defining success by whether everyone (bosses, team members, fellow managers) is happy, and hence failing to challenge the status quo.
  • Feeling de-motivated. I have had friends lament that when they became middle managers, they felt removed from the real groundwork, but not high enough to influence decisions. They lost their motivation to challenge the status quo.

Three Important Questions for Middle Managers (and their bosses)

It would be a natural point for me to go into how an organisation should select, train and reward middle managers. In the past, such articles have left me feeling validated but disempowered, as it leaves the action to the organisation – and who knows how long it will take.

As middle managers, we have agency. I’d hence like to address middle managers who are aware that they are in a Day 2 organization and are possibly perpetuating Day 2 practices. What questions can you ask yourself, and have conversations with your boss and team about? Three tips:

First, where exactly am I creating new value for my organisation?

This seems like an obvious question, but we need to be very ruthless in holding ourselves to an answer. “Keeping the peace”, or “making my boss and team happy” are bad answers that busy people can easily default to.

What are your objectives and how are you adding to them? As a middle manager, you have a wider scope than a team member, and your value could come in a variety of forms, including:

  • Taking ownership of an issue that falls between departmental lines. Take on the “start-up cost” until everyone is on-board. For example, put together a short think-piece that outlines the issue you want to tackle, and why it would be beneficial all around if different teams to got involved. Use it as a starting point to rally people across departments, and eventually bring it to upper management for endorsement and resourcing. When I became a middle manager, I realized I was uniquely positioned to take the lead on such issues, as I had greater ability to cross inter-departmental lines.
  • Examining a process that does not work, and proposing an alternative. I read this lovely article on Linkedin about the prevalence of bad systems, and why they are allowed to persist. The problem is that bad systems often end up in a kind of corporate Bermuda Triangle — no one really monitors them; worse, one is empowered to change them when the need arises.” When you see a stupid process, don’t let it pass you by. I once had a boss who had this mentality of fixing bad systems. I admired her deeply. Our department had to manage hundreds of event invitations to our Ministers. For a long time, one person oversaw all these events because it was “the only way to not drop the ball”. It clearly drained her. My boss, our “czar of bad systems”, developed a tracking list which could be rotated among 3-4 people on a weekly basis, spreading the task around and allowing us to monitor follow-through far better than before.
  • Work on a development plan for your team members. HR is not a “good to do”, but an essential objective that should take up a middle manager’s work time. Everyone does it differently, but I had monthly check-ins with each team member, where we discussed where they needed to be challenged, or supported. I kept a file on their work record, training and future job aspirations. It certainly came in handy when I had to argue for their promotions and opportunities.

“But I don’t have the time!” So true. Something has to give. Most of your bosses will have a vague idea of what is important in your job (they’re too busy thinking about their own jobs), so you have to tell him/her. Proactively engage your boss on the 2-3 pieces of value you want to deliver, and why you think it is important. Use it as an opportunity to talk about what you will not be dedicating much bandwidth to i.e. I will not be responding as fast on x, y, z issues, or for x, y, z issues, my team members will report directly to you. If you are working for a boss worth his/her salt, you are guaranteed a good conversation and probably a green light. You will definitely feel more motivated.

Second, am I creating a team in my own image, or does each individual feel empowered?

Usually, people are promoted to management positions because they did well as a team member. The result can be a narcissistic impulse to make your team members perform in the same way that you do. It is also a key source of overwork – vetting and thinking about everything each team member does. I encourage middle managers, especially new ones, to break down their management job into at least two roles, and define their value differently for each.

  1. Roles where there is a legitimate need to uphold standards. In my experience, issues that fall into this category have included managing external relationships (such as a foreign university pulling out of a partnership with a Singaporean university, with implications on our students), sensitive complaints (such as allegations of sexual harassment by a Professor or teacher), or a reply to the Minister on a key policy issue (to ensure we make the best use of the Minister’s time). These are areas where a middle manager’s experience must be applied to help the team member make the right proposal.
  2. Roles where you provide one perspective, but let the team member fly. However, there are also issues where the team member should be allowed deep ownership. Proposing an overhaul of the preschool sector? Revamping communications materials for Principals following a policy announcement? Please proceed. I’ll give you my perspective, but it is up to you what you propose to our boss. In one of my favorite jobs, my bosses were very conscious about giving us autonomy. Ministers and even the Deputy Prime Minister would call the “lowest level” staff directly, and we never felt hesitant to make our arguments.

Again, be clear to your own boss how you see your role in the different projects under you. It helps to be transparent with your team members about this too, so that they can hold you accountable if you become a micro-manager or if you’re not providing enough guidance. I’ve treasured the times my team members have said “hey Karen, we need to talk about your involvement in this project.”

If you get this right, you will also be better able to manage your time. Type 1 issues will command more of your bandwidth than Type 2. Ultimately, you want to train your team to the point where your role is largely Type 2. The more your team can fly, the more bandwidth you have. Both you and them will feel more motivated when you have that autonomy.

Third, how often do I disagree and commit, compared to having my team disagree and commit?

In his article, Jeff Bezos gave an example about how he strongly disagreed with a team’s proposal, and though their discussions did not change his mind, he committed strongly to their proposal. I was impressed – in typical organizations, the bulk of “disagreeing and committing” is by team members, not team leaders.

As middle managers or leaders of any form, we should ask ourselves how often we disagree and commit to our team members, compared to the other way around. It is a reflection of how empowered our teams are (and hence how well we are using the precious human resources we hire). It is also a proxy for how innovative our team’s culture is.


If you feel like you work in a “Day 2” organization, I believe you have the agency to bring about change, and I hope that by reflecting on these three questions, you will have some idea of how to push your team towards “Day 1”. I write about this as a fellow learner in the journey towards good leadership. Many of these lessons were the result of making painful mistakes, observing others’ strengths and weaknesses, getting feedback from my bosses and team and reflecting deeply on my own practice of leadership. I would love to hear your experiences as well.