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Alex Jones

I lead teams at the intersection of strategy and design. Autodidact. Polymath. Barbecue acolyte. I start fires (the good kind).

Managing and Teams

Leaders, stop giving permission

Instead, build an environment where they actively take responsibility.

Many books about management and countless leadership coaches exhort us to “give people permission to act” or “give people permission to fail”. That sounds good, and the statements are well-intentioned, but giving permission is not leadership, it’s simply a different way to wield authority while maintaining control.

Giving permission isn’t good enough — you must craft an environment where teams and individuals are fully empowered to act.

Better than that — they’re expected to act.

But, what if they make the wrong decision?!

Yep, that’ll happen. Failure is a real possibility. Then again, making all the right choices doesn’t guarantee success in a competitive environment either.

Telling people that they have permission means that they still derive all of their authority from you. They aren’t empowered, they’re merely borrowing yours.

That’s not good enough.

Pro-tip: give people a bit more responsibility than you’re comfortable with. You’ll be pleasantly surprised more often than not.

Now, you (we) are accountable for the decisions of our teams. But, so are the people on our teams, and they should have the right to make hard calls, lay out their choices and defend the paths they choose.

It should be expected that they make hard calls.

They shouldn’t do it in a vacuum (that’s where we come in). Their responsibility includes knowing how and when to use the resources, knowledge, and energy of everyone at hand.

But they get to make the call.

It can be scary, especially if you see failure looming, but we only get to step in if something will be a catastrophic mistake. And the truth is, wrong choices will almost never be anywhere close to that point. A little painful perhaps, but that’s good pain.

That’s the pain we all learn from.

You aren’t shedding all responsibility

There are times where you do need to clearly communicate that a decision isn’t theirs to make. After all, you’re in your role because you have the information and experience needed for tough calls. Be clear in those cases. Solicit their thoughts and then bring them along for the ride so that they learn why you did what you did.

It’s important to recognize that there’s a graduated scale of responsibility.

For example, if you’re hiring a new team member, you, as the hiring manager are ultimately accountable for choosing who gets the offer. The interviewing team should provide input and insight into that decision, but they don’t get to make it. You’re on the hook for that one.

On the other hand, if one of your managers is hiring for her team, it’s her call to make, not yours.

It’s important to recognize that there’s a graduated scale of responsibility. An Associate Designer doesn’t have the experience to make the calls of a Senior Designer. A Developer may not have the knowledge to architect an entirely new system, and likely shouldn’t be setting the go-to-market strategy. You need to know your team and set expectations accordingly.

How to craft the right environment

This is where the hard work comes in. To do this right requires that you spend countless hours, days and months modeling the behavior you want. You have to explicitly create opportunities for success within your team by getting out of the way. Here are some tips:

Visibly delegate

The most important decision you can make is to hand decisions off to people on your team and to build the right environment, you need to ensure that your team sees that you trust another with it.

Say you’re in a planning meeting, explicitly ask a team member to make the call: “Marissa, can you please research that aspect and decide which tool we should adopt?”

Clearly communicate your expectations

You can’t just toss a decision to someone on your team, you need to ensure they understand exactly what is needed and by when. They also need to know what resources are available to help.

For example: “Marissa, can you please research that aspect and decide which tool we should adopt by next Friday? Cameron helped us drive adoption for the last platform, so she’d likely have some good insight, and of course, I’m happy to help if needed.”

Appreciate the work your team picks up

And not just in your head. Make sure your team, your colleagues and your boss know that people on your team are stepping up. This isn’t about praise, though that may be a part of it. Instead, the goals are to elevate the decision maker in the eyes of the full team and reinforce the environment that you’re building.

While it may be in a team meeting, a one-on-one with your boss or an offhand conversation over lunch, saying something like “Marissa’s taking point on that one, so you should connect with her.” It may not sound like much, but it communicates a huge amount of trust and respect.

Remember that the projects don’t have to be big

It’s easy to get bogged down thinking about what you can and can’t hand off. But here’s the thing, there are a ton of small decisions that others can make, which naturally fall into your lap.

So yeah, while you do need to allow your team members to make bigger decisions, providing them the opportunity to make the smaller decisions can go a long way too.

For example, “Morgan, thanks for taking point on unifying our style guide. While you’re pulling it all together, please make a call on the name for this component and let us know what it is.”

Acknowledge (maybe even celebrate) lessons learned from failure

The ol’ “give them permission to fail” is not something you can really do. Telling people they have permission may sound like a trap to some folks or a business platitude worthy of being printed on an “inspirational” poster to be hung in the breakroom.

Plus, if you have a high performing team (I hope you do!), they likely won’t give themselves permission to fail, much less look to you for it.

Instead, we need to model failure as an opportunity to learn and iterate. And transforming failure into opportunity starts with us. As a leader, you need to visibly acknowledge your mistakes and explain what you’ve learned from them.

And you need to do this repeatedly: “Hey everyone, I messed up on that last round of interviews. I made the decision to extend the offer before getting your feedback. Luckily we all agreed, but that was a big miss on my part. Next time I’ll be sure we get together and talk through our candidates.”

The next layer is encouraging your senior team members to do the same, to model the behavior for the rest of the team and show that failure isn’t paired with punishment.

With responsibility comes freedom

Delegating decisions frees you up to work on the bigger picture, solving the more significant challenges, while simultaneously providing opportunities to your team for growth.

And there’s no stronger indication to someone on your team that they’re growing than for you to tell them “I trust your call on this. Let me know how I can help.”

As a leader, you’re expected to make key decisions. That’s why you have the title and that’s why they give you the paycheck. Some of those decisions come down to trusting your team to make many of those decisions. You’ll likely be surprised when they make a different call than you would have, only to find that it was better than your take.

Embrace that. It shows tremendous growth for the team and for you as a leader. Over time, you should be helping each person on the team to make better, and bigger decisions.

That’s true leadership.

P.S. your best and brightest are already doing this, whether you know it or not.

Photos by Priscilla Du Preez & LinkedIn Sales Navigator on Unsplash

Questions for my new boss

Woman shaking hands in office

For the vast majority of us, new bosses come along every so often. Maybe we move to a new team within a company, or we’re promoted into a new role (yay!) or we hop to another company.

Conversely, our boss may be promoted, choose to add a layer of management within the team or leave the company.

Change is a constant and there’s not much we can do about that. But, we can work to quickly understand the post-change lay of the land.

With a new boss comes a serious shift in our day-to-day routine, requiring a new set of relationship dynamics to navigate, so it’s worth spending time and energy figuring it all out early.

While there’ are a lot of questions that come with any new boss (how do we communicate, what do you expect of me, how will you help me grow?) , here are some specific to my experience leading Design teams.

I like to cut to the chase to understand how my boss looks at my team, her organization, the business and how they all interconnect. Along those lines, here are some of the areas I want to learn early on, either through direct questions or observations. Often following the direct question with long term observations to see if she “walks the walk”.

Does she view UX/design as important in its own right?

This is obviously critical—I want to know if the Design team is expected to make deep contributions and thus will be involved throughout the product definition process, or will we be brought in to make things look good, with no opportunity to drive the business forward.

Does she consider good design to be a competitive advantage, or at least table stakes?

If not, that’s a huge red flag, especially fi the current work is less than impressive. Even in the world of enterprise software, great design can move the needle. I’ve seen it act as a key differentiator on a few key deals over my career.

If good design isn’t important, I’ll be battling low morale, team turnover and constant budget battles, not to mention work that I won’t be nearly as proud of as I’d like.

How does she want us to spend our time and how does she plan to measure the value of our work?

Does she want me to show business value/ROI directly tied to design activities? If if she has any preconceived expectations, how does she think about measuring that return on investment? I want to understand if those expectations are objectively measurable and realistic given the current state of things (and what I think the future will hold).

Where does she draw the line between Design and Product Management?

There isn’t a hard line here—anyone who says there is, sets up the team for a lot of frustration. Instead, I’m looking to see a collaborative approach with some shared understandings that some decisions are firmly in the PM’s realm, while others fall into ours. Everything in-between is a negotiation, and I want to be sure we’re on the same footing when those debates arise.

Does she want Design involved in the Sales process?

A lot of companies assume the work of the Product Design/User Experience team ends with the product rolling into production. Truly successful ones recognize that supporting Marketing and Sales in the customer acquisition process provides a wealth of benefit to all involved.

Designers gain a deeper understanding of prospects and customers, as well as the rough spots of the product and pitches that we wouldn’t see otherwise. Sales and Marketing have a chance to gain a deeper understanding of why something is designed as it is and the opportunity to influence future wins.

Wrapping it up with an eye on the future

I also set a reminder for myself, which pops up after six months, to prompt me to reflect on how I’m feeling. Sometimes I can dismiss it and move ahead, other times, it’s a sign that I need to decide if it’s time for me to move on or push for change.

On a side note, while these questions are critical for leaders of Design teams, every Designer also benefits when asking these questions, even if only to themselves. Pay attention to how your team is positioned within the company and keep that top of mind as you build your career.

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Photo by rawpixel on Unsplash, modified by me.

Why are companies scared of “junior” people?

A little while back, I was asked this question by someone looking for their first design job: “why do companies fear hiring “junior” people?”

Oof.

That’s a tough one. Both because “fear” is a strong word, and because yes, a lot of teams don’t want to hire junior people.

Putting aside whether “fear” is too strong a word, here are the areas of concern I’ve seen raised about hiring someone without experience.

Junior people require more time

This is the underlying theme for all of these answers. Time is a precious commodity, and junior folks require a lot of it from their managers and colleagues. That’s not a bad thing,when structured well, but it is a thing that hiring managers think about.

Given the workload and overall team resources, there may not be enough time to invest.

Training is an investment

Photo illustration of manager helping out colleague with code

Hiring anyone to fill a role is already an investment in time and energy from a lot of people on the team. No matter the new person’s experience, they’re new to this team, it’s shorthand, processes, and tools. They have to learn how this team works.

Someone kicking off their career significantly compounds that effort. Colleagues and managers have to fill in the gaps between what the new hire was taught and the reality in professional life.

In this situation, one manager plus one new employee doesn’t equal two. You’re pretty lucky if it equals one and a half for the first three or six months.

It’s an upfront investment by the manager that she hopes will pay dividends down the line.

It will be significantly longer before they produce at a high level

Hiring tends to happen when a team is overburdened. Either they lost someone they need to replace, or they have so much work that adding a new person justifies the expense.

In those situations, a manager is pretty motivated to get someone in who can hit the ground running and make an impact. As noted above, that’s not going to happen with someone lacking experience.

Reviewing and coaching them on their work

Photo illustration of manager pointing to team member's screen

We all need another set of eyes to help us with our work, no matter our experience level. But, people new to the field need a lot more as they have yet to build a foundation of experience. Terms that are easily understood after six months are new concepts. Why something is done in a specific way has to be explained, even though it’s shorthand for the rest of the team.

Most new people will get there, but it takes time and effort for all involved.

Having to teach them how to have a job

It may sound odd, but sometimes a manager ends up having to teach someone the basic expectations that come with the professional world:. what it means to be dependable, how to communicate, how to present oneself or even that showing up on time matters.

This doesn’t happen often, but it’s a huge amount of effort and frustration to have conversations that frankly, most managers don’t feel like they should need to have. If they’ve been down that road before, they may be less likely to do so again.

It’s hard to judge past work when it all comes from a classroom

Add to the time investment, a portfolio that is made up of class projects or conceptual redesigns doesn’t provide the same level of insight as one filled with professional work. When hiring for a junior role, the manager is looking for someone with the potential to grow in the manner the team will need over time. That’s a big bet to place with so little information.

Sometimes a team needs experience

A manager’s job revolves around serving her team well. A key part of that is ensuring it has the right makeup of skills and levels of experience. The workload that they’re facing may well require that a new hire comes in with experience, possibly very specific experience.

Alternatively, she may recognize that the current team is unbalanced, requiring someone with more experience to ensure it functions smoothly. There may well be a gap in the middle of a team, which has some junior people and some senior people, but few, or no people in the middle.

So, how do you work with this reality..?

Photo illustration of two professional women speaking

This post is not meant to discourage you; quite the opposite in fact. Knowing and acknowledging these fears can help you improve your odds. Demonstrating that you know how to have a job and that you’re aware that you’ll need the team’s time can set you apart. Taking the time to build a portfolio with real client work will have an impact as well.

So, think about the fears people have when hiring someone new, just as you would think about the challenges and goals when building a product, or designing a brochure for a client. Shape your conversations, resume, and portfolio to address the concerns and you could well move further ahead of the pack.

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Original photos by Mimi Thian, rawpixel, Monica Melton and NESA by Makerson Unsplash, modified by me.

Office hours: the powerful design tool you aren’t using (yet)

Make your team available so you improve your work, build connections and extend your influence.

It's all about collaboration

One of the practices that our Design team has put in place (and was recently expanded to include Product Managers!) is holding regular “Office Hours”, where we proactively make ourselves available to the rest of the company. We go to the heart of the office — the lunchroom, so we’re in a central spot and no one feels like they’re bugging us. We make ourselves known so everyone can see that we’re open to answer questions, hear feedback or talk through ideas. The laptops are there to show work in progress or walk through a problematic area.

Quick aside: this works just as well for the “team of one”, so there’s nothing keeping you from doing this if you’re the only Designer in your office.

Why we hold “office hours”

Once you get beyond a handful of people, it’s impossible for everyone in a company to be aware of, and contribute to making an awesome product. It’s understandable — people are busy and likely aren’t even aware of what the Designers, Developers or Product Managers are working on. Conversely, it isn’t easy for us to stay on top of recent Customer Support trends, feedback to Account Management teams or reasons that Sales lost a potential customer to a competitor. That’s no good.

Destroy all silos!

While you may have some processes to help address those issues, there’s nothing like building relationships to hear about it earlier and more often. When we connect in a friendly manner, reliably and in real-time, we build our reputation as people who care about our colleagues and our customers. We show up to knock down useless silos. ’Cause who wants those around?

Predictable office hours build relationships with our coworkers throughout the company. They build trust and provide new paths to communicate. If you genuinely listen and collaborate, you’ll see your team’s influence increase, helping you to nudge the company towards a design-driven mindset. Also, you no longer have that awkward hallway nod to someone you’ve worked with but never talked with. They’re probably pretty interesting.

This is in addition to other methods of connecting with people throughout the company and should not be the only way people talk to Designers or provide feedback. We also set up roundtables with other teams and actively reach out for one-on-one sessions when we can.

Collaboration

Design is not a solo endeavor. We crave context and challenges to our assumptions to produce something that serves the people who use it. By making ourselves proactively available, we invite others in to help us see the wider picture. We also gain insight into the small changes that we can weave into projects as we go to improve the experience, allowing us to make an impact with little-to-no additional work (which is awesome, right? Right).

Talking to people pays off

Now, we know everyone has an opinion on design. It’s a common gripe that surfaces when we get feedback that we aren’t ready for and likely disagree with. Hearing those opinions, whether or not we take them is a part of the job. And of course, just as often, Designers get frustrated when they learn salient information after the work is done. So…” ugh, everyone has an opinion” meets up with “why didn’t anyone tell me that?!”

We know we don’t know everything, we spend hours researching solutions, patterns and ideas, so the most valuable thing we can do is to open our work up for others to question and challenge. By asking for feedback, we demonstrate that we value input from non-Designers.

Why not actively seek it out early, when we’re ready for it and there’s time to make a material impact? (Hint: there’s no reason not to!)

Designers know we don’t know everything, we spend hours researching solutions, patterns, and ideas, so the most valuable thing we can do is to open our work up for others to question and challenge. By asking for feedback from people who know our customers and industry, we learn, while demonstrating that we value input from non-Designers and they, in turn, see the value we bring to the business. Plus, we make a better product for our customers — it’s the ol’ Michael Scott “win-win-win” scenario!

Some questions we ask

  • Are there any areas that seem to frustrate customers?
  • Can you tell me about the people who use our product? What’s their world like? What challenges are they trying to solve?
  • If there is one thing we could fix right now, what should it be?
  • Ooh, where’d you get those gummi bears?!

Teaching

These sessions are by no means a one-way street of feedback. Designers have the opportunity to give back by sharing what they know and the reasons behind our decisions. Our co-workers aren’t likely to hear about our rationale, constraints, and goals in any other forum, not to mention just how much we debate teeny tine details within the team. We have an opportunity to share tools, practices and thought patterns that can be applied beyond our team, and we’ll volunteer to help them do just that.

Office Hours also provide a unique opportunity for people interested in our field to learn more. It’ a safe first step for those who may want to be a Designer down the road, but don’t know where to start. We’ve all been there. It’s no fun, especially for the shy or those in underrepresented groups. It also provides folks on our team an opportunity to grow through mentorship. So yeah, let’s jump in and answer some questions!

It’s Easy, So Long as You Schedule It

There really isn’t much work involved. All you need to do is:

  1. Set up a recurring time — ideally by sending an optional calendar invite to the rest of the office, making sure your team knows their participation is expected, even if no one shows up (they will in time)
  2. Send a reminder or two — drop a couple of notes in shared communication channels ahead of time, the first a couple of days ahead, the second on the morning of the event (you can likely automate this easily)
  3. Show up, ready to collaborate — bonus points if you bring treats to share

chedule your Office Hours on a recurring basis (monthly works for us, weekly might be better for you), it allows the rest of the office the opportunity to block the time to join, even if only for a few minutes. This can be important for customer support groups, who have to be on the phones at specific times. Since they have the closest ties to the humans who use our work, we better cater to them. Everyone else benefits as they can schedule around it if they want to join.

Also, commit to at least six months of these up front. No one may show up to the first few. That’s alright. They’ll notice after a while — and continued reminders from you!

So, when are you going to set up your office hours?

Interviewing – Up, Down & All Around

How I interview people for my team, peers in other teams and my potential boss

Hiring is the manager’s most important responsibility. The results of the process and the effort put in will make or break our team.

Every great manager I’ve known can proudly recount their best hires and walk you through how they blossomed. Those same managers also have stories where they failed by missing an indicator, breezing through the process, or going against their best judgment. And they can tell you about the resulting sleepless nights, stressful conversations and ruined team dynamics.

So, I’ll say it again—hiring is the manager’s most important responsibility. And it is a skill we should all be constantly working to improve. There is nothing innate about it.

In this piece, I’ll provide a high-level overview of how I interview people at different stages in their careers, taking their current role and the one they’re applying for into account.

I do not claim to be a hiring expert. I’ve hired some amazing people over the years and I’ve made some mistakes. But, I’ve done my best to examine the good and the bad to constantly improve how I interview and who I choose to hire or recommend. Feel free to take and adapt as much of this as is useful for you, and if you have questions or suggestions, please let me know.

Interviewing people who are new to the field

The number one factor that I look for is potential (as I noted in a previous piece about hiring junior designers). No matter the level of the role or the person’s years of experience, I want to know how they’ll grow within the team and what types of responsibilities they’ll likely take on over time. If I bring someone in as an Associate Designer, I want to have a feel for how long it may take until we’ll trust them to own the design for a significant area. If I were to hire a Product Manager, I want to have a feel for their ability to take on multiple products in time. Or if it’s a Dev Manager, I’ll dig into whether I feel this person will be able to build and manage a larger team, eventually managing other managers.

It’s less about where this person has been compared to where I think they can go.

work + attitude + drive = potential

  • Their work – does their experience to date provide a strong foundation for future growth? Does it demonstrate unique skills?
  • Their attitude – are they positive? Not in a happy go lucky way, rather do they view challenges as opportunities?
  • Their drive – Are they motivated to learn and solve challenges? Are they excited about crafting a product that will help people? Did they revisit work that they weren’t happy with after the assignment ended?

The search to understand potential guides my entire process. From the first view of their resume through the in-person interviews, I’m trying to understand if this person is someone that I’ll need to nudge forward or if I’ll be running to keep up.

Six questions I ask people looking to join my team

Of the projects you’ve worked on, which are you most proud of?

This is a great way to kick off the conversation as it leads on a positive note and gives me a view as to how the candidate thinks. It often segues well into the next question as many people are most proud of their hardest projects, which drove them to learn and improve.

Which was the most challenging?

This is one of the most important questions I ask. The candidate’s answer provides insight into where the candidate feels the most challenged and their level of self-awareness. The specific challenge is rarely important. What I’m looking for is how they recognized that they were facing an uphill battle, how they sized it up and how they achieved success.

If you could redo one of your projects, which would it be and what would you change?

We all have examples of projects where there just wasn’t enough time or we weren’t as skilled as we wished. This question provides a view into how they’ve had to handle tradeoffs when reality meets creativity.

Please provide an example that shows where you successfully made the case for your idea. What was the opposing idea?

This strikes to the heart of communication and influence. A lot of our work is subjective, so it’s important that a candidate be able to show why she’s made certain choices clearly to those she works with. The followup question looks to see if she took the time to understand the opposing viewpoints or just pushed ahead.

Can you show me an example where your idea wasn’t used?

Following up from the last question, I want to understand how the candidate handles setbacks and whether she recognizes that good ideas can come from many angles. It also provides a view into collaboration and individual versus team orientation.

What do you want to learn next?

I love to know what people are excited about and the gaps in their skillsets thatchy want to fill. It also highlights their natural level of curiosity.

Interviewing potential peers

When I’m interviewing someone who’ll work closely with me on different team, I focus on the skills needed to be successful in their job and how they like to work with others (what does a PM think the Designer’s role should be? How does an Engineering Director view the working relationship between Development, Product Management and Design etc.). I’m want to understand:

Do they know the job?

If they’re interviewing for a Product Management role, can they handle it in our environment? Do they understand what they would and wouldn’t be accountable for? Have they worked in similar environments and made a positive impact?

If they’re interviewing for a leadership role, I want to know if they lead in a manner consistent with our culture (leaders serve their team, ensure their people can grow, and hold their team and themselves accountable).

Do they play well with others?

Their ability to collaborate and help their team and the large org is more important than most of the bullets on their resume. Diving into their experience handling challenges and navigating professional relationships sheds light on how they interact. I want to see them credit their team instead of focusing on their own wins.

Would they fill gaps beyond the job description?

A unique combination of skills, experience or perspective can help this person drive the company forward, so if I spot an interesting area beyond the job description I like to dig in. For example, a PM who comes from a different industry and is particularly data-oriented may see something in a wholly different light when reviewing our usage analytics. She may raise and answer questions we hadn’t thought to ask.

Five questions I ask potential peers:

Most of my questions are role-specific but there are some that apply across a wide swath of candidates.

Why are you interested in this role and company?

I want to know if they did their research and which areas from that research and any previous conversations are particularly enticing. Ideally, they demonstrate that they are running toward this opportunity and not away from their current situation.

What’s the biggest frustration you deal with as a [their current role/role interviewing for]?

This helps me understand the level at which they’re currently working and helps to uncover some innate preferences or biases. Answers may range from technical/tactical roadblocks to communication and collaboration issues. How they communicate these frustrations is critical. Do they fall into griping about other people or do they acknowledge that there is a frustrating situation and shift into how they handle the frustration in a smooth manner?

How do you work with [other teams]? Where do you see overlap and where are their clear lines of responsibility? How do you navigate those gray areas?

We all have to work with other teams that may have similar or opposing goals. In many cases, lines that were once well defined have become fuzzy. Designers are far more involved in product strategy than they were five years ago and some Developers have insightful views into usability, so understanding how this candidate navigates those waters and how she collaborates is important. In some cases, people want to hold tight to strict role definitions and responsibilities, which raises a flag for me.

Can you tell me about someone you’ve helped in your career?

There’s no right answer to this question, though there is definitely a wrong one: “nobody”.

What do you want to learn next?

This question is as important for a peer as for anyone who could join my team.

Interviewing my potential boss or someone “up the chain”

I’ve interviewed potential bosses a number of times from both sides of the table. The first few times were…weird, admittedly. The shift in dynamic took me a bit to get used to, but as I gained experienced, I became comfortable asking hard questions and digging in. I now know that I can only be successful working for someone who expects and values being challenged (in the right way at the right time), so I look for that in my potential boss along with several other factors. I want to know:

Our dynamic

  • Do they expect to be challenged on their assumptions and will they provide perspective and justification for their opinions?
  • Do they communicate well?
  • Will they hold their team (and me) accountable?
  • Will they provide me the feedback that I need to hear when I need to hear it?
  • What can I and those on my team learn from them? (This is hugely important)
  • Will they trust me to execute?

Their potential and plan for growth

  • What does their career path look like and how do they aim to achieve their next step?
  • How will their growth likely impact our team and the company?
  • How does that path map with what I think our team and company need?
  • Is there anything that I might be able to teach them?

The impact of hiring them

  • Does it feel like they have a grip on what they’d be walking into, at least in rough terms?
  • Have they faced similar situations in the past and did they manage them well?
  • Will they guide everyone involved appropriately? Do I think they’ll be able to manage up as well as manage down, representing our team well and shielding it where necessary?
  • Where is their ego based? Is it in the success of themselves or the success of their team?

Eight questions I ask potential bosses:

What role do you see [my team] play in [the ___ organization]?

For example, “what is Design’s role within the Product org?” This question gets to the heart of whether we’re going to be aligned in our worldview. If their answer is significantly different than what I think it should be, I’ll dig in to better understand their thoughts and determine if I may be missing something. If they view the landscape in a manner similar to mine, I’ll probe for any differences to see how they may help my team grow.

Have you helped a company shift from [our current size/scale] to [the next significant level up]? What strategy and tactics have worked for you?

When hiring a senior leader into a growing company, there are typically known areas that need improvement, often related to scaling up to the next level (revenue, company size etc.).

Have you helped solve [a specific pressing challenge our team/company is facing]?

Similar to the scaling question, I like to develop an understanding of where their experience can be directly applied to solve some of the big challenges my team is currently facing. I’m also curious if their solution is similar to what I would expect or significantly different than I think we should go.

How do you structure and interact with your direct team?

I want to know if they’re going to be particularly hands-on or hands-off and the rhythms and processes they like to follow. I also want to understand what changes would likely come were they to join the team.

How will you measure my success and that of my team?

Knowing up front how they view my role and that of the team is critical. This question gets to the heart of their understanding. If the types of metrics they apply match mine, we’re in a good spot, but if they’re significantly different, we need to dig in further. For example, as a leader of a Design team, I would not expect to be measured on revenue but would on customer satisfaction or the ability to hire and train effective teams.

From what you’ve heard so far, what sounds like it is working well and where do you think you can help us improve?

This provides a view into what they’ve learned from their research and previous conversations as well as their understanding of the challenges we face. Their response in terms of how they can help us improve helps me to understand the unique skills they can bring to the table and/or correct any misunderstandings.

How would you spend your first 90 days?

I want to know if they have a plan before walking in the door. My hope is that they have a rough outline of the types of things they will do, but that they aim to hold off on major changes until they’ve had the opportunity to observe and learn from their interactions and the day-to-day reality.

What concerns do you have about the company or role?

The answers to this question can be fascinating , revealing a lot about the candidate. It provides an opportunity to provide more detail and reduce, if not eliminate the concern.

On Interviewing

A few general notes on interviewing:

  • I aim to ask the same set of questions to every candidate for a role with a few additional ones added in based on the conversation. This helps provide an even playing field for candidates.
  • There is rarely ever a “right” answer in my questions as so much depends on the specific person, their background and the role we’re trying to fill.
  • As I noted in T-Triple-C, I have some key attributes I look for in every interview, no matter the role and no matter which side of the table I’m on.

Thanks

I’d like to wrap up by thanking Vitorio for suggesting this topic. He’s been an active member of the Austin design community for a long time and routinely introduces alternate perspectives and thoughtful responses to discussions.

Photo of “The Bobs” from Office Space from 20th Century Fox

If you have thoughts, questions or suggestions, please weigh in. I’d love to hear them!

“You Don’t Have the Experience for this Role…Let’s Talk!”

Embracing Junior Designers Who Apply for Roles that Require Experience

Hiring designers (or developers) here in Austin is a paradoxical combo of too many and not enough. If you’re looking for people new to the field, you can spend days going through applicant portfolios. If you’re looking for someone with experience, you’ll spend that time weeding out those same portfolios to find people who have the experience you’re seeking. Now, I personally feel that too many companies miss out on the opportunity of hiring talented folks as they only hire experienced designers. Their unwillingness to invest in the people new to our field is a disservice to the candidates and the team.

Lucky for me, that also means I have more opportunities to hire new designers with huge potential.

So, back to the quandary — designers without experience applying for a role that requires experience. Yes, sometimes we need someone who’s worked as a designer before (or developer or writer etc.), but there can be an opportunity to bring in someone new to the field — so long as a couple of key aspects are covered with them upfront.

Level Set With Them, They’ll Appreciate It

I’ve had this conversation countless times now. During my initial phone interview, before I start diving into my questions, but after I’ve given them a chance to ask theirs, I lay out our career path and levels. I explain that people new to the field start as Associates and I walk through the role, explaining the responsibilities and expectations, noting what is not expected of someone new to the field. I then explain that more senior designers have a very real responsibility to mentor those with less experience. We talk about the day-to-day and our team practices like our weekly design feedback sessions so I can explain that the title doesn’t indicate hierarchy — everyone shares work and is everyone open to feedback from each person on the team, including from a brand new Associate Designer.

99 times out of 100 the response is something like “This is exactly what I need! I haven’t heard of any other companies doing this…” This is both gratifying and disheartening. I love that they’re excited, but frustrated that it isn’t common practice.

Once this is explained to them, the candidate’s energy level immediately shifts and the way they participate, answer and asks questions is noticeably more comfortable and confident. You can tell that they are more open and willing to ask what may seem like a “basic” question. They’re more comfortable sharing what they’re excited about and where they’re challenged, prompting new conversation threads.

Structure Your Team Properly, They’ll Appreciate It Too

It’s all well and good to have that conversation, but then you need to back it up. This is where your more senior folk come in. They must be approachable and available to help the new designer beyond the initial week or two (think months and years — it’s ongoing). This is a critical part of their job, and they need to know that. They also need to be afforded the time and protection to do it, so timelines or project loads may shift accordingly. A new designer needs to be paired with an experienced one, even if they’re working on different aspects of a feature or different projects altogether.

This might seem like a non-starter if you’re slammed, but the investment up front pays off huge in the long run. Your new people gain experience and learn from the team’s best, building loyalty. Your experienced people get to build and flex those mentoring muscles which is highly rewarding.

And it all starts with a simple conversation that may seem hard at first, but will be appreciated by the people you want on your team.

Photo by Willian Justen de Vasconcellos on Unsplash