FounderFuel: The simple questions that can set you free as a startup leader

As entrepreneurs we often find ourselves in the role of leader by default. We set out with a business vision in mind, inspire people to join us and on the journey we inevitably inherit this role as the team grows. The question then becomes, what kind of leader do you want to be, and what will get the best out of your team?

Do you even identify with the term leader? Often the idea of a leader conjures up grandiose images of world leaders and inspiring visionaries. As such, many founders don’t identify with it, preferring the idea of a manager or team lead instead… but if we strip out the semantics, we are still in the role of leader. We’re responsible for people, their payroll, seen as the font of all knowledge and the decider of significant decisions, and it comes with a significant weight of responsibility. All this without ever having the time or chance to consider what kind of leader we want to be or what behaviours can create a truly empowered high-performing team.

“If your actions inspire others to dream more, learn more, do more and become more, you are a leader”

6th US president John Quincy Adams

Leading to get the best from your team

Rationally we all know that we need our teams to be empowered and autonomous in order to scale, but in practise it’s tough to do as an entrepreneur.

Pioneering Harvard organizational behaviourist, J. Richard Hackman uncovered a set of “enabling conditions” that leaders can create to get the best out of their teams. He poses two critical questions to drive real team autonomy:

  • Have the ends been specified? (the ‘what’ or goal)
  • Have the means been specified? (the ‘how’)

This creates a useful check for whether we are empowering people or straying into micro-managing. If we micro-manage too much we disempower and demotivate, which leads to wasted resources and ultimately team turnover.

This is all especially tough as a founding leader though and the challenge is two-fold:

  1. There is a natural tendency for others to look to us for the answers to problems and to make the final decision.
  2. As founders we’re born problem-solvers – it’s in our nature to want to fix a problem plus we’re pretty good at it (and it’s fair to say we probably have a clear view of what the ‘right’ solution is too).

So to get the best from our people and keep them motivated, we have to resist these natural tendencies. We want to define what we want as a result from our teams (the End) and not define how to do it (the Means). That means letting people solve their own challenges, make their own decisions and that takes both trust, tenacity, and willpower as a leader!

In a Cornell University study of 320 small businesses where half granted their people autonomy and half didn’t, the businesses that used autonomy grew at four times the rate of the control-oriented businesses.

The simple questions to empower your team

The good news is that building a coaching-style and a few simple questions into your arsenal can transform your ability to empower others. For this, our founders use the Empowerment Cycle. It is one of our most accessible coaching frameworks because it can be integrated easily into day-to-day conversations as a startup leader. It is also very flexible, enabling you to pick up at various points in the cycle depending on situation or experience level of who you’re working with.

Coaching-style: Asking questions that help people discover the answers that are right for them

When someone comes to you for an answer or brings a problem, simply work through the cycle, pushing for their recommendation whilst supporting their development:

weare3Sixty Empowerment Cycle for founders and startup leaders


weare3Sixty Empowerment Cycle for founders and startup leaders

For best results, flex the model to the situation: If someone brings a challenge, drop in at the Description stage; if they want a decision, ask for their Recommendation; if an individual or team is overwhelmed by options, unite them around an agreed Goal. As part of this coaching-style conversation, seek to understand any genuine barriers, then be an enabler in helping them break these down.

Do you have time not to?

With the fast-paced schedule of a founder it is hard to make time (and even find the energy) to employ a coaching-style at times. But if we don’t help our team members build their skills and encourage them to have autonomy over the challenges they encounter, they’ll keep coming back for answers instead of finding their own solutions. Eventually we become the bottleneck as the founder and this hand-holding kills productivity and creativity.

By contrast, a coaching-style helps to agree goals, unlock the barriers and motivate all involved. This question-based coaching style empowers others to seek their own solutions and by doing so, they tend to be much more motivated by the solutions because they came up with them, so it’s win-win all round.

It is a mindset shift as founders though – we’re so used to having to fix things – sometimes the biggest barrier to experimenting with this approach is our own belief that we know the right answer.

Tips to practise with:

It might feel awkward at first – like all new things, it isn’t easy – especially as we often have a desire to dive straight in with a solution – but with practise it becomes natural. It might take slightly more time at first (much like delegating!) but many will embrace the new approach quickly and start coming with recommendations rather than problems, letting you take a more strategic approach to leading.

Flex style consciously: You can be directive and offer advice as part of the Cycle, but do it consciously. You can build in your ideas later in the Options section and be specific about what you need, and what good looks like, when agreeing actions in the Action Plan section.

Always ask before advice: Quieten your urge to help or fix, aim for a 4:1 ratio of asking questions over offering advice, and only offer Options after they have offered some first.

Avoid starting questions with Why: Why can feel like an accusation, triggering defensive rationalisation. Swap for How and What questions instead, it really helps.

Written by Christina Richardson, founder at weare3Sixty
Founder coach & trainer | Startup exec-team coach | FounderCircle® creator & head-coach. Passionate about sustainable founder performance, wellbeing and the leadership transition from founder to C-suite.

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At weare3Sixty we believe in supporting the humans behind the world’s ambitious startups and our mission is to make sure that every founder and startup leader in the ecosystem has the support and skills to reach their full potential as resilient, high-performing leaders.

Here you’ll find 1:1 founder coaching, team coaching and team training all dedicated to the unique ride that is starting up and scaling up. Not only that, with our group-coaching FounderCircles® you’ll be surrounded by hundreds of other talented founders on the journey too – all committed to fuelling themselves, their teams and each other for the ride.

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