Part I: Creative Leadership

Maximizing one-on-ones

The creative industry, and the creatives who inhabit it, have a wealth of resources at our disposal.

Want to learn more about user behaviors? Thousands of blog posts by industry experts break down tested research around the smallest UI nuances. Not sure about the best way to texturize hair in Illustrator? There’s hundreds of YouTube videos on that. Widely available and affordable/Open Source design resources are one of the many great aspects of working and learning in this industry.

However, for all of the tools that exist to learn technical skills, we lack the tools to learn and discuss what creative leadership looks like. A handful of written resources do exist: Harvest Business Review and 99u, but on the by and large, creative leaders are left to learn (or not to learn) the skills to develop future design leaders. On occasion, I have enlightening discussions at events or hear a profound speakers on the subject but these experiences and articles are exceptions rather than the norm.

As creative leaders, we need to discuss the leadership aspects of our jobs more. Instead of learning from just our individual experiences, how can we cultivate a culture where we have more conversations around the work as it pertains to the people? What methodologies do we as creative leaders find most effective?

I am by no means asserting that I am a single-handed expert on creative leadership. Through this series, however, I do hope I can put what I’m doing to start this conversations with my peers.

One-on-ones 📌

One-on-ones (or 1:1s) were something new to me when I started agency life. For those not familiar: A one-on-one is a standing meeting (typically weekly) for two people to regularly connect.

One-on-ones are intended to be regularly scheduled, closed-door conversations between managers and direct reports (but they can also extend to leadership or project peers). At their best, they provide a safe space to discuss goals, challenges, and feedback. At their worst, they can be viewed as a weekly rote update or worse, a standing calendar invite that does not happen at all.

Below are ways I’ve found to maximize my 1:1s as a manager to being an effective use of both parties’ time. I’m always adapting and hoping to find ways to adjust 1:1s to work for the individuals on my team.

1. Logistics are key: Set a weekly caedence and time allotment in a private place, then make sure it happens 📌

Part of the efficacy of a 1:1 is holding it with regularity. Weekly seems to be a good cadence for my past teams (monthly or bimonthly makes sense for peripheral team members). It is consistent enough to make meaningful progress on projects without being overbearing.

The private place (whether that be digitally or physically) should be a no-brainer, but sometimes sensitive information about challenges with other team members, or personal details are discussed. It’s important that your team members feel comfortable. Setting the 1:1 in a closed-door setting will help facilitate that.

It’s easier for the “busier” person of the two to de-prioritize 1:1s. I try very hard to not cancel/move 1:1s. To me, this commitment is a manifestation of how important this individual is and how important their work is to our collective success.

If I do have to move or to cancel it, I try to communicate it early, take the initiative to reschedule/hold our next meeting, and apologize. I expect the same respect in return.

2. Ensure that it's a two-way conversation 📌

As an ambivert, this is something I try to be extra mindful about: Give space for more introverted, quieter team members to share. Sometimes it takes time and awkward silence to happen, but it always will. If it doesn’t, you might not be asking the right questions…which leads to:

3. Ask open-ended questions 📌

Forcing yourself out of the habit of asking yes/no questions will force your team member to prioritize the information they think is most meaningful and avoid rote-update type answers.

4. Adjust based on team members' communication styles and needs 📌

Not every team member can or should be treated exactly the same. Some team members want to get down to business and not waste time with pleasantries. Other team members prefer to ease into business—and appreciate the discussion around weekends and life beyond work.

A tool we used at a previous job is the TTI Communication Assessment. Every team member takes a test that helps provide context for how they communicate and prefer others to communicate back. The entire team has access to one another’s profiles. I try to keep these preferences in mind to adjust how I speak to each employee.

5. Keep the big picture in mind 📌

As the manager (especially if you’re a manager of managers) it’s important that you keep the priority and task clear. It is our job to ensure that the team member is making progress on larger quarterly and annual goals. If a team member is spending a lot of time on something that doesn’t align with their ultimate career trajectory goals, then it’s your job to redirect and re-prioritize to get them back on track.

6. Set clear directions then hold the person accountable with written documentation 📌

I find discontent happens most often with team members when they have unclear directions or are not held consistently accountable (then, unexpectedly held accountable).

For each team member, we keep an shared Google Doc where I take ongoing notes during the 1:1. If we agree on an action item for either of us, it’s marked as such and we ensure we check in on those items during the following 1:1. Particularly, since those action items don’t usually pertain to hard deliverables, it holds us both accountable when having a difficult conversation or checking on back-burner tasks.

The 1:1 document is supremely helpful at the end of year review when it’s easy to forget what challenges and wins each team member has faced throughout the year. I use the 1:1 document to cite specific examples to support these growth plans.

7. Use 1:1s to provide critical and positive feedback in a timely manner 📌

Lack of consistent feedback is a common challenge for employees (and warrants its own blog post). Studies consistently show that employees crave more feedback (both positive and productive) than they receive, and that employees who receive consistent feedback are more satisfied and engaged.

The 1:1 provides all of the groundwork for providing feedback: Private setting for the candid discussion, consistently held. I think the primary reason people avoid giving feedback is that it can feel awkward.

As the manager, if you provide feedback consistently (and elicit feedback yourself), it’s going to feel more normal to you and your team member to give and to receive feedback week over week.

Doing so in the 1:1 also reveals trends. If someone is consistently receiving feedback in the same areas and isn’t making improvement, you might need a plan in place or more active mediation. Alternatively, if someone received feedback a few times and made progress, that’s also good to call to attention.

What have you found successful in your 1:1s? I’d love to hear what methods you have found to be effective for you.