On a recent episode of Finding Our Way, Jesse and I spoke with Tim Kieschnick. I worked with Tim for about a year, and learned a ton from our collaboration. He’s an interesting cat—he worked at Kaiser Permanente for 30 years (until retirement), and in that time helped establish their web presence, UX as a practice, service design, and HCD/Design Thinking/Design Sprints. He’s a reflective practitioner, and through his experience developed two frameworks which I have in turn used in my thought partnership practice with design leaders. I was eager for him to share his wisdom on our podcast.

The 3Ps of the Leadership Ceiling

A little over a year ago, at my urging (so I could refer to it without feeling like I was plagiarizing), Tim posted an introduction to The Leadership Ceiling. (some of what I write here will repeat what’s over there, but in my words.) At heart, it’s a simple construct: Leaders create a conceptual ceiling above which their organization cannot rise. Tim identifies three ceilings:

Purpose

Why does this organization exist? How is that purpose articulated? Are we driving toward output, or outcomes? How does our purpose inspire, connecting people with their higher, better selves?

People

Who is in this organization? What is the caliber of contributor? And, are we creating a truly people-centered organization that enables those folks to deliver at their best? 

Process

How is the work getting done? Does our process bog us down, or lift us up? How are we coordinating across functions? Are people spread too thin, across too many initiatives, or are they able to maintain focus and commitment? Are teams empowered to practice a process that is ‘fit for purpose,’ or is there an imposed standard way of doing things that cannot be deviated from?

(This is reminiscent of what Daniel Pink identified in Drive, in terms of what it takes to motivate people: provide them Autonomy (process), Mastery (people), and Purpose.)

In my experience, I don’t see three ceilings, rather one ceiling that is a product of how these three factors intersect. In my work with design leaders, looking at the intersection has proven helpful, because it illuminates why there’s cognitive dissonance between the message they’re getting from their leadership, and why the work doesn’t meet their expectations. 

The diagram to the right shows my take on this aspect, which is that the Leadership Ceiling is set by which ever factor is lowest. 

For instance, I’ve supported a number of banks and insurance services firms. And nearly all of them have high-minded aspirations for their business, with mission statements about empowering people’s financial wellbeing, or improving the health of all Americans. And these firms will also have committed to providing a much more conscientious work environment that encourages bringing your whole self, and stresses values of psychological safety and vulnerability.

But these large legacy organizations are bogged down in process, for reasons including bureaucracy, poor organization design, unwillingness to truly empower teams, people spread too thin across too many workstreams, etc. 

And so, the Leadership Ceiling is established by that lowest factor. And the design leaders I work with, who may have been sold on a company’s vision and culture, then struggle when they realize that for all that high-and-mighty talk, their ability to deliver is severely hamstrung by a lack of attention to process. 

The ABC’s of The Leadership Ceiling

Once you understand the height of a Leadership Ceiling, then you have to figure out your relationship to it. Tim uses an ABC mnemonic to think through what you can do:

 

Diagram of the ABC of The Leadership Ceiling from Tim’s website.

You can try to work Above the ceiling

This approach is pretty common for designers, particularly new to an organization, who see their job as to ‘fix’ whatever came before, or to realize a bold new innovative vision. And they may see their leader’s Ceiling, and perhaps engaged in some effort where they bumped their head on the ceiling, and then see their job as the innovative iconoclast to work above the ceiling, to show to the rest of the org just how great it can be. 

This never works. You might get some time to play in that rarefied air, but inevitably the leader’s Ceiling does its thing, often in the form of the Leader being frustrated that the designer isn’t doing what was expected of them, instead pursuing some quixotic endeavor that was bound to go nowhere.

So, most of us end up working Below the ceiling

We realize that we are constrained by the leader’s ceiling, and focus our efforts there. The dream is to have a leader with a high ceiling across all 3Ps, providing all kinds of headroom to innovate and grow. But most of us find ourselves below a ceiling lower than our liking, and so we have to make a choice:

We can Bail. We may believe that we’ll never reach our potential, or that work will be endlessly frustrating, and given our limited time on this planet, we want to focus our energies elsewhere. (This has been what I do. This model has helped me realize that I have little tolerance for working under a low, or even medium-height, ceiling.)

We can Bide our time. We make the best of the situation in front of us, delivering excellence within the leader’s constraints. Biding may sound defeatist, but it shouldn’t be perceived as settling. It can be a smart and pragmatic strategy of getting things ready for when the time comes and either our leader raises the ceiling, or is replaced by someone with a higher ceiling. In the podcast, we talked to Tim about telehealth, which Kaiser Permanente had been pursuing for 25 years. And if you were passionate about telehealth, you were likely frustrated, because it never caught on the way you felt it should—the organization wouldn’t invest in it and the membership didn’t seem to appreciate the convenience. 
And then 2020 happens, the world goes on lockdown, and that causes the Ceiling to be raised on telehealth. And all those folks who had been biding their time, waiting for the moment, are now center-stage.

Some bold souls may seek to Change the ceiling

As Tim puts it, this “is not for the faint of heart.” But if you are frustrated by the height of the ceiling, and you’re not content working Below it, and you’re committed to the organizational cause and so you won’t just Bail, you can try to change the ceiling. This requires diagnosing just what is depressing the ceiling, developing an argument and a plan for raising the ceiling, and then doing the hard work of education and evangelism to persuade leaders to change the ceiling. This is particularly tricky, because those leaders, over their career, have received a lot of confirming feedback about the rightness of their decisions, and now someone within their org is going to tell them that they’ve got it wrong? So, it requires delicate, incisive, and persistent communication to figure out what stories resonate with the leader and encourage them to evolve their view. 

I’m so grateful Tim spoke with us, and driving broader awareness of this framework. I’ve found it quite useful in my work helping design leaders succeed, and I’d love to hear (or read) how it works for you. 

Every design manager knows there’s an intense war for talent.  It’s been going on for the past 15 years, and has definitely ratcheted up in the past 12-18 months. 

Last year, I supported one team that grew from 14 in March to over 40 by the end of the year. This wasn’t some sexy tech company—it was enterprise SaaS supporting HR. I point this out because, even in with all the competition, it’s quite possible to scale an organization. The issue, which I’ve seen over and over again for years, is that most design orgs are just bad at recruiting and hiring, getting in their own ways. Here are the top mistakes that I’ve seen. 

Hiring Managers don’t devote the necessary time

Hiring Managers are busy people. Their attention is pulled in many directions. They are expected to lead their team, provide creative vision, manage the individuals, partner with cross-functional peers, roll up their sleeves and do the work, oh, yeah, and build their team. That last item gets deferred, as it doesn’t have the urgency of their other responsibilities. As such, many Hiring Managers find themselves in this cycle:

Depicts the vicious hiring cycle

Perhaps the single most impactful thing a Hiring Manager can do is protect their time for recruiting and hiring. When active, expect to spend about 4 hours per week per open headcount—this accounts for time spent sourcing, reaching out to prospective candidates, initial conversations to gauge interest, deeper conversations once someone applies, and the background stuff around planning and preparing others to support the hiring process. 

Over-reliance on Recruiters

When I counsel design executives and their leadership teams about recruiting and hiring practices, I often get a variant of the reply, “Isn’t that the Recruiter’s job?” The short answer is: No. 

This isn’t to say you shouldn’t develop a strong partnership with your Recruiting team. But, I’ve seen, again and again, that when Design Leaders rely on a separate Recruiting team, particularly for sourcing potential candidates, their efforts come up short. 

The Design Org needs to own their recruiting and hiring practices and processes. The Recruiting partners are their to support you, not do your job for you. 

Under-reliance on the rest of the Design org

While Hiring Managers need to be the engine that drives recruiting and hiring, this doesn’t mean they operate as lone wolves, expected to do everything on their own. Hiring Managers must rely on support from others in the Design organization, specifically:

  • Their manager — to help them protect their time, and manage the relationships with peers who may be upset that the Hiring Manager is focused on recruiting, and not “the work.”
  • Their team — Hiring Managers should engage their team members in sourcing, gauging interest, and interviewing. Not only is this an example of “many hands make light work” (ok, lighter work), I have found that passive candidates (i.e., those not actively looking to change jobs) are often more receptive to outreach from another designer, in a way that they are not from a Design Manager, and definitely not from a Recruiter.
  • Design Operations — Any scaling organization should have a “PeopleOps” person specific for Design, and among their responsibilities is maintaining a set of robust tools to support the recruiting process: job descriptions, career and levels frameworks, question banks, and assessment rubrics. 

Insufficient articulation of the role(s) to be hired

Hiring Managers know they need people, and often take an existing job description, lightly revise it, and post it. They rarely do the diligence to figure out what they actually need in the role. This hinders the recruiting process, as it becomes apparent, through conversations with candidates and colleagues, that there is not a shared understanding of the profile we seek to hire. 

This is a classic example of “measure twice, cut once.” A little more work upfront will lead to far less time spent down the line. 

One tool I’ve begun to see great promise in is the Thank You Note, as posited by Jared Spool. This is an “artifact from the future,” where the Hiring Manager drafts a memo thanking the person for what they’ve accomplished in their first year. Putting yourself in that ‘year ahead’ mindset, while forcing yourself to be specific, results in essentially drafting the job description. 

Cavalier recruiting processes that ignore known best practices

This frustrates me more than any other aspect, because solid practices for recruiting are not mysteries, but teams neglect them. Hiring Managers resort to what they’ve done in the past, and everyone wonders why it’s so hard to find good people. 

Processes that are too lengthy or too brief

For a client I supported in 2016, I recommended shortening the interview day (which takes place after initial phone screens) to “5 hours, 6 hours most.” When I recently re-read that, had I been sipping a beverage, I would have done a spit-take. Because while that amount of time is too long, I’m now seeing teams that spend 2 hours with a candidate, total, before making a hiring decision, driven by the need to ‘act fast’ in this competitive market.

In my experience, there’s a “Goldilocks” scenario that works for most design/research/content hires:

  • Two 30-45 minute phone screens, one conducted by the hiring manager to get a sense of the candidate as a professional, another by a team member digging in to the specifics of their craft
  • Panel Presentation + four 1:1s, taking about 2.5-3.5 hours

You need to spend enough time to feel confident in the ‘signal’ you’re getting. But too much time leads to diminishing returns. 

Adversarial stances with candidates

Many hiring managers (and their broader recruiting context) approach engaging candidates in an adversarial way, where the candidate has to ‘prove themselves’ worthy of consideration. Fuck that masculine posturing bullshit. Your company isn’t so great that it can act as if they’re deigning to speak with someone.

I’ve also heard Hiring Managers say that they don’t want to provide too much information (see the next item), because they felt part of the process was the candidate to figure out what’s expected. Recruiting processes shouldn’t be the conversational equivalent of an escape room, where the candidate solves the puzzle of ‘how do I get hired?”

And, for my sake, just stop with the design exercises.  No, really.

No preparation for candidates or interview panelists

Perhaps because of the time constraints mentioned at the outset, I often find Hiring Managers (and Recruiters) do almost nothing to prepare either the candidates or the interview panelists about the process and what’s expected of them. 

With candidates, sometimes it’s a matter of the prior point on adversarial stances, but often it’s just thoughtlessness. Apart from blocking time on their calendar, candidates often have no idea what to expect from conversation to conversation. 

With panelists, often, they learn about an interview when a slot is dropped on their calendar, with no context, not even a resume or LinkedIn profile. 

Candidates should be provided extensive preparation for the process. How long it will take; what the steps are; how to shape their portfolio presentation; whom they will be meeting and what topics will be addressed. We want to best know the candidate, and that means enabling them to present their best self.

Panelists should be coordinated such that each has a topic area that they dig into, and a set of questions to draw from. This avoids needless duplication across 1:1 interviews, and ensures a broader understanding of the candidate. 

Gut-level judgment of candidates

Throughout the process, the assessments of candidates are typically superficial and gut-driven. Hiring Managers and panelists may take notes, but often there’s no standard by which to make a judgment, and so hiring decisions are based solely on feeling, rather than a considered judgment, placed against a robust profile of the role.

This gets back to the issue shared earlier, where Hiring Managers insufficiently articulate the profile of a desired candidate, so people don’t have a clear frame of reference for their judgment. This can lead to a couple of different problematic outcomes:

  • the endless searching for some kind of unicorn who satisfies everyone
  • offers extended to a candidate that everyone likes, but is actually not suited to the role: for example, hiring someone as a Lead Designer because everyone thinks highly of their design skills, but not enough was done to assess their leadership characteristics

A lack of up-front clarity also contributes to implicit bias, favoring candidates who ‘look the part,’ whether or not they’re best suited. 

Assessment rubrics for each stage of the process should be clearly defined ahead of time. I’ve published a tool I’ve used to support portfolio reviews. You’ll need to come up with your own for other stages. 

With solid assessment rubrics, hiring decisions become much clearer and with reduced bias. You know when someone is qualified, and you’re confident in making an offer. 

And there’s more…

What’s shared here are the top mistakes that, in my view, contribute the most to poor recruiting outcomes. But by no means are they the only issues that commonly arise. Others include:

  • Poorly written job descriptions, typically too vague, boilerplate, and littered with non-inclusive language that discourages qualified applicants
  • Unclear or undefined levels framework, so judgments about job requirements, and then candidate aptitude, are made without any frame of reference
  • Sourcing practices that don’t go beyond posting a job to a LinkedIn profile and hoping for the best
  • Waiting too long to address the compensation conversation, only to find out in the offer stage that your salary band doesn’t meet candidate expectations
  • Lack of appreciation for reference checks, the only tool in this process that  engages people who have actually worked with the candidate

If this sounds like a lot, that’s because it is

Generally,  design orgs simply have not treated recruiting and hiring with the focus, attention, planning, and effort that it deserves. It is somehow just expected to get done. 

I find the story I told at the beginning, of a team going from 14 to 40 in a year, to be illustrative of a path forward. I was supporting that team, and probably spending ~10-15 hours a week on various activities that support recruiting (career ladders, job descriptions, working with recruiters, sourcing, interviews, etc.) By having a senior person in a People Ops-like role, who wasn’t weighed down with explicit management responsibility, who could develop materials to support recruiting practices, and also drive the effort in hiring key leadership roles, this team was able to scale quickly and with quality. Most teams aren’t willing to make such an up-front investment, instead hopeful that they can get by with what they have. What I’ve seen, though, is that orgs that make that investment, realize a worthwhile return. 

From a VP of Design I work with:

“I had to have an intense conversation with someone on my team, who is struggling with the shift from Design Manager to Design Director. The Product Lead this Director works with has started reaching out to me again. When I dug into it with her, I found that she’s still doing the thing that Product Managers love, getting into the nitty-gritty details. But the Product Lead is still waiting for a vision statement, a hypothesis around where the experience could be going. She went too deep too fast, and hadn’t gotten alignment on strategic direction.”

When working with executive design leaders across organizations, I often hear something along these lines. Their Managers and Directors don’t know how to best spend their time, and where to focus their attention. Interestingly, I hear something similar from C-level people about design executives—they’re too focused on their team, and not the organization as a whole.

What many design leaders don’t understand is just how much their role changes, in particular, the relationships they need to have, as they advance in their career. 

Design Manager

A Design Manager is someone relatively new to formal leadership, and has people reporting into them, anywhere from 3 to 8 (any more than that, and the Manager will be overwhelmed). 

Diagram of how a manager spends their timeTheir primary orientation is downward. They’re focused on getting the most out of the team the manage, making sure they’re delivering on expectations in terms of addressing problems and upholding quality.

Their secondary orientation is sideways, working both with Design Manager peers to drive coherence across teams, and working with cross-functional peers (Product Management, Engineering), to coordinate and plan delivery efforts.

Design Director

When we promote a Design Manager to become Design Director, we often don’t communicate how this is a fundamentally different job than the one they had before. As the quote that started this post shows, many new Directors resort to the practices that helped them succeed as a Manager, but those will get in the way of their performance as a Director. 

Diagram of how a Design Director spends their timeA Design Director’s primary orientation is sideways, and not only that it’s mostly outside of Design. An effective Design Director should be spending more of their time and energy working with non-design peers and other stakeholders than with any other kind of colleague.

Their secondary orientation is downward, with a focus on managing their Managers. Their job isn’t to get into the nitty-gritty themselves, but to provide guidance and mentorship for their reports. Directors are also crucial for establishing the management culture and philosophy for their teams. But they shouldn’t need to spend anywhere near the time they used to in managing down, because, well, they have managers to handle that. 

Lastly, a Director will spend a small portion of their time managing up, to their VP and non-design leadership, keeping them apprised of what’s happening in their world, and learning overarching strategy and vision in order to make sure their organization is aligned with global goals. 

Design Executive (S/VP of Design)

When talking to CEOs, their primary concern about Design Executives is that they see themselves as a Design Leader first and an Organizational Leader second. CEOs expect Design Executives to see their cross-functional peers as their “first team.” with the design organization as their second.

How a VP spends their timeAnd in terms of time spent, it goes even farther than that. The Design Team should be where a Design Executive spends the least amount of time. Their primary orientation is sideways, toward their executive peers. This is about planning and strategy for the organization, identifying opportunities for the business and how their coordinated teams can realize them.

Their secondary orientation is up and out. It may seem counterintuitive that an executive would spend so much time engaging with a small number of even more senior executives, but that’s the reality. That’s your key audience. They’re the ones who are needed to support the plans of the Design Executive and their peers, to commit the resources necessary. “Out” may mean executive leaders outside your direct reporting chain, and in some environments it may mean key customers or partners. As a Design Executive, you now represent the company in a variety of contexts, both internally and externally.

A high-performing Design Executive should spend their least amount of time focused on matters within their Design Organization. It may take a while to get to this point—it requires a strong Design Leadership team, and effective operational practices around recruiting and hiring, staffing, performance management, quality standards, etc. But, really, a Design Executive shouldn’t need to spend much time orienting downward, because they should be able to rely on their org to get stuff done.