Starting up? 5 lessons I’ve learned

Many friends have recently asked me for advice on starting up new roles. New roles come in many forms, whether you are tasked to set up a new function in an organization, transform an existing team to do new work, or if you decided to set up your own start-up. The common thread is that no one has done what you’re tasked to do, so you have no precedent to reference.

I’ve been in these roles to varying extents, and here is the gist of what I’ve learned/shared with my friends.

As a caveat, these lessons might apply more to folks who started their careers in more traditional backgrounds and are now breaking out into more original, start-up roles; less to lifelong entrepreneurs.

  1. Give yourself the license to “not know”

High achievers pride ourselves on figuring everything out quickly. In the first week, or first month of the new role, we expect to have a clear and coherent strategy. We expect that everyone else understands what we are doing and is supportive. We expect to have figured out the solution to this problem. It seems absurd and most of us would never expect these of others. Yet if we are honest, we expect these of ourselves.

The result: the resistance, confusion and lack of clarity you inevitably face in this new role sets off a strain of the following narrative: “I must be the wrong person for this job”; “I must have been crazy to leave what I was good at to do this”; and it may even get to “I should get out of this right now, and cut my losses.” Not a good place to be, I’m sure many of you would agree.

The most important thing when starting out is to give yourself the license to “not know”.

  • I do not know the best strategy to achieve this objective – hell, maybe the objective was the wrong one to begin with and it’s my job to call that out.
  • I do not know which stakeholders I need to involve and how to get them to align with me.
  • I do not know what this role will look like in 6 months’ time.
  • I do not know how I am going to manage this particularly snarky team member.

I do not know many things, but you know what? Nobody knows. There is no “correct” answer. My boss (or if you are a start-up founder, your customer) is not hiding the answer and waiting to slap me on the wrist if you get it wrong. He/she does not know how to solve the problem, and I am here to figure it out. Lean into the “not knowing”. Shut down the inner critic who says you should “know by now”.

This brings me to the next point.

  1. Set your learning agenda, not just your performance agenda

I just want to do this job well”. “I want to get results”. When high achievers start unprecedented roles, their goals are typically performance-driven.

Unfortunately, only having a performance agenda can be very discouraging. When you are in an unprecedented role, the gap between where you are and the results you wish to achieve is much wider than in a steady-state role. It makes total sense: when you are doing something unprecedented, you don’t yet have clarity about the different steps in the chain-link to success [you may not even know how to define success]. In contrast, when you are in an existing function, a lot has already been done to establish this chain-link, and you can focus on delivering results.

How do you cope with this? I often advise friends or coaching clients to develop a learning agenda to complement their performance agenda. Setting small, achievable learning goals will keep you on track to performance and help you battle through the inevitable discouragement.

First, what is your professional learning agenda? A useful exercise I’ve learned: in the first months of a new role, don’t just keep a “to-do” list. Also keep a notebook of questions – things you wished that *someone* had an answer to. As part of your professional learning agenda, put some timelines on these questions. By month 1, I would like to have answered these questions or at least have some clarity around them. Similarly, for months 3, 6 and 9. Review your questions periodically; pose them to different people you work with. With this tool, you can be assured that you are building the chain links to success, without burdening yourself with the unnecessary pressure of reaching the highest objective immediately.

Second, what is your personal learning agenda? What do I, as a person (not a worker), want to learn from this experience? In the chaos of starting up, we often forget that we chose this path because we wanted to change, to learn. If you left your consultant job for a start-up, perhaps you wanted to learn the ins and outs of operationalizing change. If you left a cushy local role to set up operations in a new market, perhaps you wanted to learn about operating cross-culturally. If you decided to take on a larger team, perhaps you wanted to learn about people management.

Whatever it is, don’t lose sight of why you chose to take on this role, and what you personally wanted to learn from it. Keep yourself accountable to your personal learning agenda, whatever is happening on the performance front. This has often helped me press through the most difficult starting up months. Of course, if you realize you are getting nowhere in personal learning, it should also trigger a re-evaluation!

  1. Don’t take resistance personally –  put on your “consultant hat” often

When you are in an unprecedented role, you will run up against resistance. It’s almost tautological if you think about it. When starting something new, you and a few others might see the gap, but most people don’t yet – if not, your job would likely already have been done!

The majority of people you work with might feel that your work is irrelevant at best, and at worst encroaching into their territory, creating more work for them, making them look bad. Even if some agree with your objectives, they might disagree on how you should do it. Depending on workplace culture, critiques can often become personal in nature, casting aspersions on your character, motivations, intelligence, judgment and so forth.

The idea is to not take it personally – but how? I’ve been in several situations like this, and one of the most useful pieces of advice I heard was “put on your consultant’s hat”. When coming into a messy situation, a consultant’s advantage is often that they are not personally invested. They see things from an organizational point of view.

Instead of asking personal questions like “why are these people so resistant to change?” or “what’s wrong with me, why can’t I get buy in?”, ask organizational questions like “What conversations need to take place to alleviate this situation, and how can I facilitate them?”, “if my voice alone is insufficient, who else in the organization is well-positioned to be an advocate for my strategy?”. One of my ex-consultant friends suggests: “What help can your boss or peers provide for you to be more effective sooner – be it mandate, role clarity, or warm introductions? Help them help you – you are the closest to the situation, you know what you need, so take time to analyse the situation and ask for the help you need”.

Putting on a consultant’s hat (and taking out the personal lens) helps me focus on changing what I can about others’ responses, and leaving what I cannot. It also inclines me towards constructive and kind behaviours since I’m neither villainizing myself or others.

  1. Aim for quick wins, embrace opportunism and experiments

I mentioned that in the early days, you don’t always know what success looks like, let alone how to be successful. Instead of going for big wins that demonstrate that you are a resounding success, focus instead on small, “quick wins”. A good “quick win” demonstrates the potential of your new solution, and very importantly – how it can benefit the organization AND other teams. It makes others more likely to want to work with you AND give you resources; an important chain-link to larger success.

In my experience, embracing opportunism and an experimental mindset are essential to scoring early quick wins. For example, instead of aiming for the best partners or the most impactful problems to begin with, aim to find just one or two groups who have an urgent need. Work quickly with them to establish the problem, define, and measure success. Try your new method. Experiment. Measure. Publicize. Tweak your solution and repeat.

This sounds very intuitive to people who grew up as entrepreneurs. But if you came from a corporate, steady-state role, it is extremely unintuitive. You might feel the urge to have a coherent strategy before you begin or to only go for the solution that has a clear path to scalability. Resist this – starting up is all about trying and learning, and there is a whole lot of opportunism in finding the right partners to begin with.

Small, quick wins are what will help you gain confidence, and bootstrap your way to better strategies and bigger “successes”.

For example, when I was setting up a new strategic communications team in the Ministry of Education, no one quite understood what “strategic comms” was and how it was different from “regular” comms. A good quick win was to find an issue where the traditional comms model was not working, evidenced by huge pushback from educators on the policy. We defined success as a shift from educators being critics to educators being advocates, and redesigned the communications processes to enable it. Once we could demonstrate success, we had more business than we could handle.

Recently, I was asked to bring back tech talent for Singapore from the Silicon Valley. I told my network that I wanted to figure out how best to approach this problem. A few months later in Dec 2017, Facebook reached out on Linkedin, asking if we could collaborate to attract talent to Singapore. I said yes immediately: in fact, could we hold an event at Facebook Menlo Park in March 2018, since several key Singaporean tech personalities would be flying to the Silicon Valley at the time? A very small group of us got to work, and within 2 months, drew top-notch speakers and 700 registrants – three to four times the number we were expecting. Feedback was overwhelmingly positive. We spent so little money that it surprised everyone at home. Most importantly, we got what we needed to bootstrap towards even more effective strategies: data on who these tech talents were, what were their timeframes for relocation, their skills, passions and how they needed to be served.

Snapshot from our first Tech Forum in March 2018
  1. Build networks outside your team and organization

It’s easy to lose your bearings when you’re starting something new. You will face resistance at work. Your family might question your decision to do this, when “life was so much easier in your previous role”. You more-than-occasionally might wonder if you are crazy; if this idea is worth pursuing; if it’s the right time to give up.

When you are starting up, it is essential to build new networks outside your regular circles, especially in two areas:

  • With people who are walking (or who have walked) the same journey of starting up. They will give you a reference point as to which parts of your experience are normal, and which parts you perhaps should be concerned about (like if you are going off the rails, or if you really should give up instead of press on). They can also share what worked for them in overcoming the challenges of starting up. You can even look within your organization for these people, as one friend suggests: “Are there others in the broader organization who might be in similar positions, though not necessarily in the same function? What did they do to navigate the situation? Can you extrapolate from their situation?”


  • With people who are tackling similar problems to you in adjacent domains or industries. From my experience, these people end up being your source of professional ideas, contacts and partners in experiments. Friends asked me how I was invited to speak at top tech conferences like CES, SXSW and become a faculty member at Singularity University so quickly, starting with zero network in the Silicon Valley. The short answer is that I met a few like-minded Americans in the early weeks. We chatted over common interests, both personal and professional. I shared with them my objectives, challenges and ideas. We became friends and genuinely enjoyed each other’s company. As and when I met a connection or saw an article which would interest them, I shared it. Over time, this small group became great advocates for my objectives. They referred valuable connections; they pulled me onto panels they were speaking on so we could debate on stage just as we debated in-person; they nominated me to bring Singapore’s voice on various technology issues they were working on. This network has enabled me to achieve all my other objectives more effectively.

The biggest tip here is to not be transactional in relationship-building. Approach networking building with desire to build meaningful relationships. Don’t expect something out of every person and every conversation. Be ready to put in more than you expect to get out of the relationship. Sometimes a collaboration or connection might emerge immediately, but many times you build a good relationship and wait – the outcomes will show themselves over time.

With Elliot, who I met in the first week of arriving in SF

Your views?

These are five lessons I’ve learned on how to stay sane, and succeed, in starting up new functions, teams and ventures. I’m sure many of you have more experience and insights to share. Would love to hear from you!





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