The Management Conundrum. Why Management Is Harder Than You Think – and How to Go About It

Updated: Dec 9, 2021



“100% of participants in CE’s incubation program are excellent managers.” That’s the impression one could get reviewing surveys on participants’ preferences for the two-month program. Usually, nobody thinks that we should put an emphasis on management in our courses. To be fair, there are many good resources on managing people out there. Moreover, many participants have managed staff before.

Yet management is likely one of these skills for which people overestimate their own abilities.

Not too far off the famous experiment from the 1980s according to which 8 out of 10 drivers consider themselves above average. I definitely don’t fall under the illusion that I am a better driver than average (one friend avoids getting into a car with me after a road trip in Ireland… in my defense, they drive in the left lane). But, heck, I have definitely also overestimated my management skills in the past and still learn on a daily basis. Here are some of the lessons on management we’ve learned at Charity Entrepreneurship – at times naturally, occasionally the hard way.


1. NOT EVERYONE IS THE SAME


It might be obvious, but not everybody ticks the same way. So don’t manage everyone as you want to be managed. Or don’t expect that there is one pure form of modern management that applies across the board. Instead,

use different leadership styles based on the person. ​​

Team member A might appreciate a high degree of autonomy and dislike task assignments that are too upfront (e.g. you creating a task in Asana for them). Team member B, on the other hand, may feel in limbo without a clear structure and regular check-ins. Adapt the degree of autonomy and your communications style based on your colleague. Look for verbal and nonverbal cues that indicate what leadership style a person prefers. Just being receptive to those signs can give you a lot of data to work with. Yet even more importantly, ask. Your team members usually have a very good sense of how they prefer to interact with you. This can involve the frequency and style of check-ins, the frequency and channel of your communications, and your common approach to managing tasks (what processes and apps you are utilizing). Your weekly 1:1 meeting is a good format to bring this up. An individualized approach also applies to distributing tasks among team members. Ideally, a majority of tasks assigned to someone build on their strengths and interests. Of course, your team members should have the right to grow and expand their skill set. Yet handing out tasks to someone neither interested nor well qualified to implement them is not sustainable. Consider assigning such activities to another team member, even if it defies the logic of titles or departments (e.g. a research team member helping out the operations person on a complex budgetary spreadsheet model). Finally, task load calls for a tailored setup. Alex might get easily stressed out with more than a few tasks on his shoulder at any moment. Betty might get bored if she cannot switch between tasks frequently and therefore prefers a higher task load. Several ways help you figure out the right workload. First, ask about stress levels and progress. It can also help to get a sense of how much more time they need for each task at hand. In this respect, app-based time tracking is a helpful management tool (check out e.g. Clockify or Timely). The manager gets a sense of how realistic her/his assignments are and can manage priorities better. The team member has a record of time spent which strengthens his position (to counter a question like “does this really take that long?”). The quality of the work might be an even stronger indicator of workload but should be coupled with the individual’s feedback and time spent. Otherwise, you might have employees that produce high-quality work but feel constantly stressed or work around the clock.


2. HAVE A PLAN


Don’t mix up a modern management style that gives your staff a lot of autonomy with a free pass to operate without a plan. Even with the most talented and autonomous staff, you are responsible for the overall strategy and implementation as a co-founder. And it is fair to assume that your average staff member needs quite a bit of input in this regard. A frequent mistake is to treat planning as something you do on the side – for instance, only when your busy schedule allows. On the contrary, ​

defining your goals and outlining the path to implement them is one of your key tasks as a manager.

You don’t want your organization to be the rocket that speeds in the wrong direction. With many options to pursue and the constant uncertainty around their likelihood of success, planning is hard and takes time. Allocate sufficient time and energy for it and delegate seemingly urgent day-to-day tasks to others to free up space. Don’t fall into the trap of “I wish I had time for planning but I just need to …”. Charity Entrepreneurship has published various resources on planning and decision-making, including practical examples of exploring options with spreadsheets. For a discussion on how to prioritize tasks also check out the article on productivity and task management.


3. DON’T HESITATE, DELEGATE


As the founder, the charity is your baby. You know it in and out, from high-level strategy down to the Google Spreadsheet script that cleans your database. The temptation, therefore, is to jump right into action as a new task pops up. This proactive attitude serves you well in the earliest days of your org when there is simply nobody to help out. But quickly you will be able to gather a team of staff, contractors, interns, and volunteers. Instead of carrying out most tasks, take a step back, and focus on high-level tasks such as strategy, fundraising, recruitment, and planning. The rest can and should be delegated


4. OVERCOMMUNICATE AND BE AVAILABLE


Knowing every single process at your organization bears another risk: the “Isn’t this obvious?” fallacy. As you assign tasks, remain aware that you have a much deeper context than your colleagues. A brief task description without clear examples and goal descriptions might be insufficient. Communicating a strategic change only once or twice is likely not enough to sink into your organization’s culture. This simple rule of thumb on ‘overcommunicating’ comes in handy:

When you think you have communicated something extensively, add another one or two iterations and you will likely reach an adequate level.

Another way to be a good manager is to remain available for questions and check-ins. This does not mean that you have to respond to Slack messages 24/7 within minutes. Deep work time is important and should be respected by all team members. But don’t be that busy manager that never gets back to questions or postpones weekly 1:1 meetings. This is not only demotivating at a personal level but turns you into a bottleneck for the whole organization. One of your key goals as a manager is to enable and support your staff. Being available is the first step in this direction.


5. CREATE A POSITIVE CULTURE


The One Minute Manager is one of the most succinct introductions to management. It also stands out for its positive approach to leadership. Giving positive feedback is often a much more useful strategy than criticism: ​

Providing positive feedback can guide others and amplify their strengths. So when someone does well, highlight what they did that was good, and note why you liked it. Often they will then build on that strength in other areas of their work, pre-empting your input.

Of course, this does not mean that you would not make suggestions on how your team member could improve. Yet you may want to consider shifting your ratio of positive/negative feedback in a much more positive direction. This also applies to areas of weakness, where you can put the focus on highlighting even minor improvements (instead of concentrating on the issues). At a higher level, leading by example is another expression of a positive approach to management. Instead of hoping to enforce rules through strict guidelines, the founder team shapes the organizational culture with their own behavior. This approach is more appealing and also more scalable, as culture scales with the expansion of your org to dozens or hundreds of employees. If you, for instance, want to instill a practice of showing up on time for meetings and respecting deadlines, make sure to be the first person to adhere to this.


6. IMPLEMENT COACHING-STYLE MANAGEMENT


Who likes to feel like a robot that diligently processes tasks fed by a manager? Yes, this is an exaggeration but traditional management can at worst be interpreted in such a fashion. Autonomy has always been a key contributor to happiness. This applies even more so to highly-skilled and motivated team members. So instead of structuring your relationship with an employee in a traditional way, consider implementing a coaching style. A few differences stand out:

  • A coach does not have all the answers. Often s/he is not an expert in the field of the coachee. This reflects current working arrangements where you might need to manage someone highly specialized, e.g. a developer helping you implement a database dashboard. It acknowledges that input from the staff member is often if not always superior to that of the manager.

  • A coach enables and supports someone in implementing her goals. This applies well to modern management. While you might set the general direction as the superior, the staff member should have full ownership of the sub-strategy and activities to meet the targets. The manager ensures that there are no roadblocks on the way, provides resources, and helps the other to reflect on progress towards her goals. From this perspective, the team lead works for the team member, not vice versa.

A step further in this direction are experiments in self-organization where organizations get rid of hierarchical levels or titles. One finding in this nascent field is that it does not have to be an all or nothing approach. So think twice before you scrap every seemingly outdated structure in your organization (and consider Chesterton’s Fence). More so, every organization needs to find its individual sweet spot between traditional management and self-organization. Transitions from a traditional to a more self-organized model also take quite some energy, as e.g. Danny Bürkli of staatslabor (formerly Centre for Public Impact) outlines in a series of Medium posts. One of the classics in the field is the book Reinventing Organizations by Frederic Laloux. If you are into podcasts, Leadermorphosis might be a good starting point.

If you would like to explore modern frameworks of leadership, also take a look at Ray Dalio’s Principles. His approach, in brief, is famous for a radical (and sometimes uncomfortable) approach to measuring and assessing reality and one’s own work outputs. Conscious leadership is another up-and-coming framework, practiced at companies such as Asana, and includes a deeper reflection about one’s feelings and a path towards a less self-centered life. Dalio’s Principles might come across a bit harsh for some, while conscious leadership may be a touch esoteric, but both are worth checking out.


7. HIRE LATE, FIRE EARLY


An organization is all about its staff. Yet as a key task of every manager it is worth mentioning a classic rule: hire late, fire early. This might be one of those guidelines that require experiential learning to be fully ingrained. For many of us, our general disposition goes against hiring late and firing early. Motivated young managers that we are, we tend to get overenthusiastic about expanding the team when the org grows. This can seriously affect the startup’s trajectory. Keep in mind:

  1. The culture and work ethic is critical in a small organization. Hiring too quickly increases the likelihood of bringing in people that are not conducive to the charity’s mission.

  2. Managing is harder than expected (just to reiterate this article’s punchline…) so you can stretch your leadership capacity if you grow your team too quickly.

  3. In startup mode, your program and needs are often still up in the air. As co-founders, you can quickly pivot and shift priorities as well as responsibilities. Once you bring in staff members, this gets harder. While you can and should look for generalists, you and your team member had a certain set of responsibilities in mind when starting your common journey. Radical shifts can result in the employee feeling uncomfortable or getting an incompatible task portfolio.

  4. Even if your organization is on a more stable trajectory don’t hire if you cannot clearly define the person’s duties - or if you expect someone to fulfill multiple very different roles. If you cannot clearly define someone’s work go back to the drawing board. It is your duty to be able to define a new hire’s immediate weekly tasks as well as work plan over several months. Don’t go into this with a “let’s figure out her tasks once she is on board” attitude.

  5. Don’t expect someone to be a Uomo Universale (polymath). It is usually difficult to find staff that work really well as researchers in the first six months, then become excellent operational leads and build up country programs in several locations. In sum, slow down your recruitment plans.

Okay, hire late… but fire early? Sounds harsh – doesn’t everyone deserve a second chance? Definitely. This is not to promote a hire and fire mentality. Yet as a greenhorn manager you tend to let staff go too late. There are several reasons for this. You are a nice person and don’t want to hurt anyone. You dread the difficult interpersonal interactions once things do not work out. And, unfortunately, you are super busy growing your organization. So you need every help you can get, right? Let’s not lose this person in this critical period of time. I have been there. We are not talking about cases here where new staff members need some time to get going or might only perform at 90% of what you expected. You usually only consider firing someone when it really does not work out (or you run out of funding): the person has a toxic personality, has poor work ethic, constantly makes serious mistakes, does not show any signs of improvement etc. In these cases, consider parting ways earlier than what your intuition tells you. While difficult, the firing process can still be fair and considerate.

Communicate your concerns early, give multiple opportunities to improve, and discuss potential other career avenues for that person.

Also, consider a severance package, i.e. continuing to pay a salary for a few additional months. This is a socially correct way to do it and it also avoids issues (e.g. the person seeking legal recourse or turning into an ‘opponent’).


8. HELP STAFF GROW


At a startup, there are constant fires to extinguish. As a manager, you therefore have a tendency to want your staff to be fully engaged in the critical tasks at hand. That’s fair, yet don’t forget mid- to long-term growth of your staff. While you will not be able to match the broad set of training opportunities of a large company, institute a few training opportunities. These can be modest and include affordable online courses (edX, Coursera, Udemy, etc), book clubs, and peer-learning among staff. Even more importantly, understand the direction your team member wants to develop in. Ask about this proactively in 1:1 meetings and ensure that each team member uses at least a few hours per week to develop her/his skills, for instance, by taking an accounting or coding class. Upskilling staff helps you fill managerial positions later on and makes you an attractive employer. You can also contribute actively to someone’s personal development, which is a value in itself. For these reasons, resist the temptation to limit personal development because you might fear that they move on. Losing staff members is not always easy but a natural process - and one that strengthens your organization’s network.


9. BUILD AND DOCUMENT PROCESSES


“Isn’t this what we discussed that one time over Slack?” One of the most frequent mistakes we see co-founders make is not documenting their processes sufficiently. Initially, you are often only two co-founders that communicate frequently. Heck, why would you need to write down stuff? There are, in essence, two main reasons.

  • The obvious reason is that your organization will scale and you need to onboard new staff. Going without written documentation limits your bandwidth as you are bombarded with the same questions over and over. It also results in duplication of work – for instance, someone starting a new policy/process on x when this has been defined in the past. Similarly, if you have documented processes you can also outsource them beyond your own staff, e.g. to volunteers and contractors on platforms such as Upwork.

  • Finally, and most importantly, writing down a process allows you to reflect more clearly on it, get second opinions and improve it steadily. Even the first time you bring a process on paper, you will immediately spot the potential for improvement, e.g. why does this start with Person A then go to B and then back to A; couldn’t Person A complete both tasks together?

In sum, documenting processes and turning them into standard operating procedures (SOPs) improves quality, accountability, and consistency at your org.

The basic elements of SOPs include: the person responsible, the steps necessary to complete a task, and the related deadlines. In terms of software, you can go from basic to more sophisticated:

  • Google Docs works really well to document processes. The key here is to not split up your processes into many documents and to combine where possible (e.g. Employee Handbook). Of course, one document will also not be sufficient, so make sure to have a hub (Google Doc or Spreadsheet) with a constantly updated and easily searchable/sorted list of policies with the related links. Otherwise, be ready to go Easter egg hunting on your Google Drive. You can split policies up according to a departmental (e.g. Operations), thematic (e.g. Finance), or geographic logic (e.g. India Office).

  • Task management software such as Asana works great if you need to set up workflows. There is even specialized workflow software if you need a more tailored solution (e.g. Kissflow or Process.st). There is still value in documenting the bigger picture in a Google Doc and letting the software take care of managing the daily management of processes.


10. SCALE AS A LEADER


The trajectory as a startup leader is unique. You usually start out with limited management experience and the requirement to take care of everything yourself. And within 1-2 years you might be confronted with a large organization and dramatically different expectations of you at its helm.


There is only one way to go about this:you have to scale as a leaderas your organization is scaling around you. Easier said than done, however. Your early qualities as a startup manager might actually jeopardize the more established organization. The proactive can-do attitude that suited you well in the early days may turn you into a dreaded micromanager. The quick-and-dirty implementation that allowed you to move quickly might at a later stage contribute to compliance risks (e.g. running out of cash due to poor accounting, or getting into trouble with authorities due to a lack of attention).


This table summarizes how traits that are positive in the early days may turn into liabilities later.



Positive Traits in Early Days

Potential Liabilities at Later Stage

Getting sh… done yourself

Micromanaging

Acting quickly

Compliance and liability issues

No time for management and culture

Poor culture and unhappy staff

Working extremely hard

Burnout of yourself and staff

A plan is overrated

Organization is moving into different directions due to lack of unity

Don’t hire a lot and/or don’t train a lot

Lack of talent, especially management talent

​The mitigation strategy here is not to do everything from the beginning. That is impossible as you would jeopardize your early success. Yet you have to gradually adapt to your organization’s maturity and needs. You have to move from “do most of it yourself” to “don’t do any daily management or implementation”. A good framework to think about this is working towards making yourself superfluous. Build an organization that runs well without you. The final stage of this transition would mean that you (or a new management team) mostly deal with the following high-level matters and leave everything else to others.

  • Strategy

  • High-level fundraising

  • Management of your senior team

  • Recruitment and training of senior team

  • Culture

Looks pretty different from your starting point, doesn’t it? As you steer your startup forward, plan for the occasional stop to reflect. Have you taken the necessary steps to scale up as a leader (e.g. getting an executive coach or doing psychotherapy)? Have the steps taken been successful? Do you even enjoy working at this level? The latter points to the fact that not everyone is suited for and enjoys working at all stages of an organization’s leadership. It is fine to acknowledge that and look into transition plans. At most organizations, some or all members of the co-founding team move on eventually. Your startup is your baby, but someday it'll grow up and be ready to move forward independently. But right now, you are far, far from this point, so enjoy the ride and continuous learning required as a leader.


SUMMARY


  1. Not everyone is the same – so adjust your management style to the person. Try to accommodate your employees’ preferences for task type and load, for example, and for how you communicate with each other. Remember you can always ask!

  2. Have a plan – don’t treat planning as something on the side. Defining goals and outlining the path to implement them is one of your key tasks as a manager.

  3. Don’t hesitate, delegate – focus on high-level tasks (e.g. strategy, fundraising, recruitment, planning) and delegate the rest. Delegation is often possible earlier in an org’s trajectory than generally assumed (e.g. through contractors).

  4. Overcommunicate and be available – to keep your team on the same page on everything from individual tasks to overarching strategy. Communicate and then communicate again, and maybe a bit more after that. And make sure you’re available to your employees (within reason of course!).

  5. Create a positive culture – by giving positive feedback and leading by example.

  6. Implement coaching-style management – support your team without the need to have all the answers yourself. Also look into newer management trends including self-organization, conscious leadership, and the principles methodology.

  7. Hire late, fire early – because your employees influence your whole org. Make sure you’re certain on hires. And hard as it is, as soon as you realize an employee isn’t working out, let them go in a fair and socially adequate way.

  8. Help staff grow – through training opportunities, online courses, and peer learning. Upskilling your employees benefits you both. And don’t fear talented employees leaving: think of it as expanding your network.

  9. Build and document processes – writing out standard operating procedures, for example, will ease onboarding and allow you space to reflect on how to improve your workflow.

  10. Scale as a leader – different stages of your organization require a different leadership style. From doing everything yourself as an early-stage startup, you’ll end up delegating all but high-level tasks.


READING LIST

Internal resources

  • Using a Spreadsheet to Make Good Decisions

  • Achieving Pareto Productivity: Simple Task Management and Productivity Rules that Go a Long Way

  • How to Be a People Person

External resources

  • The New One Minute Manager

  • Reinventing Organizations

  • Leadermorphosis

  • What our emerging model of self-organisation looks like

  • Conscious Leadership

  • Principles