Leading With Questions

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Leading With Questions

Leading a team, whatever the size, is a difficult task. Too often, managers resort to simply telling their team what to do instead of teaching them how to define it for themselves. They focus on directives instead of giving the team goals and empowering the team to figure out the best way to achieve them.

To effectively lead a team of highly motivated and skilled employees, these employees need to know they're operating in a realm of trust and empowerment. A very effective way to do this is to lead with questions.

Leading a team full of highly ambitious people in a creative or knowledge field—like design, product management, or software engineering—is even more complex. This complexity only grows with the size and momentum at which the team performs.

A Shift in Information

The computer and the network have democratized access to information, driving a significant shift in working style away from top-down leadership. Where in the past authority came from information asymmetry through layers of leadership, you are now more likely to see organizations where most information (internal communication, data, etc.) is available to all.

The leverage of the open availability of this information can dramatically positively affect the trajectory of a company. It has allowed many, still relatively young, technology companies to scale at a blistering pace. But the availability of this information also brings a different way of working.

Where in the past hierarchy would dictate and control the information flow to teams and individuals, now leaders need to gain the trust of their teams in an open forum. In an environment of open information, you need a level of rigor to internal communication, decision making, and leadership. To perform at the highest level and scale this performance, leadership needs to focus on trust and empowerment.

Trust and Empowerment

Many people who’ve worked with me will have heard me say: “there is a time when you hire people for their hands, and there is a time when you hire people for their brains.”

When you tell someone specifically what to do, and even worse how to do it, you ask an individual—who you hired for their skills, knowledge, traits, and behavior—to be a set of extra hands for you.

If you’re looking to build a successful team, grow your impact, or scale a business in any field of knowledge work, everything should be biased towards trust and empowerment. So how do you empower your teams? How do you empower individuals? How do you ensure that they get the things done that need to be done?

Before we get to that, let’s start with some questions:

  • How sure are you about the work that needs to get done? Do you know what success looks like?
  • Do you have absolute, 100% confidence and conviction in your direction and guidance? If not, how confident are you?
  • What information are you missing? Do you know what information you are missing, or do you not know what you may not know?

Or, said differently: do you need your teams to go out and understand the problems in front of you, identify what success could look like, and come up with a plan to get there?

In an environment with high trust and empowerment, you won’t have to lead through traditional means. Instead, progress gets made through collaboration up and down the leadership chain. More importantly, trust and empowerment work both ways. If you trust your teams and empower them to do great work, they will allow you to scale your operation. This will enable you to focus more on long-term strategy, and creates more trust upwards to your leaders.

Creating the Environment

How do you create an empowered environment built on trust? Trust works in a reciprocal manner. To create a climate of trust, you have to show people your faith in them by empowering them with an ambiguous task with clear expectations.

Here’s an oversimplified e-commerce example: you have a hunch that you are leaving money on the table because conversion isn’t optimized. The wrong way to lead would be to say: can you make the PDP (Product Detail Page) convert better? The even worse way would be to say: can you make the “Add to Cart” button bigger?

You have to extend trust to your team by asking questions: how can we improve conversion? Can you put together a list of opportunities you see? The low-hanging fruit may be entirely elsewhere, and focusing on the two PDP directives could be a complete waste of time.

What happens in this interaction?

  1. You show the team that you value them for their brain(s).
  2. You teach them the question you are asking yourself, which lives behind the directive you would have given them otherwise.
  3. You allow them to surprise you and tell you about the things you may not have known.

After the work is done, you will want to review it either asynchronously or in a meeting. (While I try to reduce meetings as much as possible, they are ideal for creating an environment of trust as they have more tone and context than written words.)

When reviewing the options, you have the perfect opportunity to show your team your thought process and how (a) you would prioritize this, or (b) what new questions this brings up for you. Likely what will happen is that you get to make decisions on part of the proposals or the direction while opening up space for more exploration.

Notice how this creates a safe space, as there is no judgment in this environment, only learning. You are directing them, but you are not telling them what to do. The level of empowerment and trust increases, and over time you can safely ask more complex questions or have more challenging conversations without hurting the team's ability to lead themselves.

Direction, Not Directives

A crucial aspect of leading a team through any discussion or review process is to see yourself mainly as the moderator, not the judge. You are part of the process; you are not above the process.

There is a straightforward approach to moderating the conversation that optimizes for empowerment but hedge against inertia. At its core, there are two essential tactics: (1) asking questions and (2) paraphrasing. Both optimize for trust and empowerment. Never, ever, start by asking a leading question.

The steps in any professional discussion are:

  1. Ask an open question (e.g., a question with an answer that goes beyond yes or no),
  2. ask a closed question (e.g., a question that has a yes or no answer),
  3. paraphrase and make a suggestion, and
  4. paraphrase and make a recommendation.

This also works in managing up, or in any direction for that matter. Not only does it scale as the organization scales, relationships based on trust compound over time and can help navigate through the most challenging moments.

What’s more, professional relationships based on this foundation can transcend a single organization and allow for long-lasting partnerships throughout roles within—or outside of—a company.

Start Small

As with all advice, things are often easier said than done. It is doubtful that you will start a behavior like this for a few weeks, and immediately it propagates throughout your whole team, organization, and business. There is even a high likelihood that only parts of the organization will be run in this way—I’ve seen this first hand.

Start small. Start with a place you have the most confidence in or an area with the least external dependencies. Some examples of my recent past have been empowering design systems at Glossier and the mobile team at Brex. Once you successfully show that you can create an environment of high trust and empowerment, you increase your own confidence, and you have examples to refer to that others can see as well.

Leading based on trust and empowerment and leading with questions can be a game-changer. It won’t happen overnight. But once the environment shifts, it will create a tailwind for everyone.

A massive thanks to [Amy Snook][1] for her editorial feedback on this.

[1]: https://www.linkedin.com/in/amy-snook-9392ba23/


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