Hiring with Precision: Identifying the Right Talent at the Right Time

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This is a podcast episode titled, Hiring with Precision: Identifying the Right Talent at the Right Time. The summary for this episode is:
Creating a talent strategy
01:33 MIN
Signals that it's time to make a hire
02:03 MIN
Prioritizing the roles to fill
01:50 MIN
Evaluating the skills of someone already in a leadership role
03:14 MIN
Tools you can leverage to evaluate performance
01:29 MIN
Building out a leadership time from startup to scaleup
02:13 MIN
Considering fractional vs. full-time
02:11 MIN
The time commitment of filling a full-time role
03:07 MIN
Keep the candidate experience in mind
01:02 MIN
What you can do right now around hiring
03:15 MIN

Holly Enneking: Thank you all so much for joining us today. I'm Holly Enneking. I'm the head of marketing here at Bolster, and I'm joined by two of my colleagues, Patti Dorsey and Cathy Hawley. If you're not familiar with Bolster, we're an executive talent marketplace that matches CEOs with senior leaders for fractional, full- time, board, and advisory roles using a combination of our experienced recruiters like Cathy and Patti, and backed up by our marketplace and platform to find exceptional talent. So today we're going to be focusing on hiring and specifically what you can be doing now to recognize when you need to hire, determining what roles you want to prioritize, and start building out a more actionable talent strategy. Before we get started, I'm going to have both Cathy and Patti introduce themselves. So Cathy, would you mind going first?

Cathy Hawley: Sure. I'm Cathy Hawley. I'm one of the co- founders of Bolster. I've been in people roles for most of my career. My last role was chief people officer of Return Path, which was about a 600- person company at the end. I now focus on a lot of different things in Bolster, including helping clients, really supporting clients, and helping them find the right talent. Patti?

Holly Enneking: Thanks. All right, Patti?

Patti Dorsey: Hi. Yeah, I'm Patti Dorsey. I'm an executive recruiter with Bolster. I've been in talent acquisition for a little over 20 years. Started out on the agency side with the Robert Half International inaudible, and then moved over into corporate recruiting soon thereafter, leading TA teams for those companies across all different industries, companies, medium- sized up to publicly traded companies. And then my most recent role was leading the strategic talent operations for a healthcare IT public company. So I joined the gig economy two years ago and that's where I met Bolster. I've been doing some executive sourcing and recruitment for them over those two years and then just this month joined permanently, so excited to be here.

Holly Enneking: Yes. Awesome. Thank you so much both of you. So let's go ahead and dive in. One thing that CEOs often hear from their investors or advisors is that they should have a talent strategy. So Patti, when you think about a talent strategy for a scaling company, what do you focus on and what are the most important considerations that someone should have in mind?

Patti Dorsey: Sure. So for a company that's scaling or really any company, a solid talent strategy is essential to its success. But first, let's talk about what that means. What is a talent strategy? That's basically a company's approach to aligning their talent to meet the goals and objectives of the company. So this includes a myriad of things: assessing the current talent, looking at any gaps, determining any learning and development needs that might be there with that existing staff, focusing on retention, building an inclusive culture. All this probably sounds familiar to you. This is really part of the employee value proposition that you're creating. So included in that is also the succession planning, branding. You want to think about how are you going to attract and hire talent? So all of these things really, Holly, are what you should take into consideration. When I think about developing that talent strategy too, you have to use data, so don't forget the data. You want to inform the development of that framework in order to increase the efficiencies as well as reduce bias and identify the best talent to bring to the organization.

Holly Enneking: Nice. So let's assume that we've got a good talent strategy. We're thinking ahead. We're thinking about all of these checks and we've got some of these right processes in place. Cathy, what are some of the signals that you think you should be looking for or keep an eye towards that might help you recognize when you need to be making a move or maybe adding someone to your executive team?

Cathy Hawley: So I'd say kind of building on the talent strategy. If you look at talent strategy specifically for the leadership team, I call it a talent roadmap or a leadership roadmap. I just step back and think about what roles do I need to cover on the executive team, who's covering them now, and what might I need to cover in the next three to five years? Mapping all that out in a really kind of... I have a simple tool for it that it belies that there's actually a lot of work that goes into figuring out what to put in there, but really looking at that can be helpful. Again, I think it's very similar to just the overall talent strategy, but it's a little more focused on the leadership team. So really starting to think about who's handling the people function today, for example, and then what level are they at and what would I need in three to five years for that function? And then I'll say the other part, that looking at what are the signs that you need somebody new, in Startup CXO, we have something at the end of every section. So every section is a different C- level role. At the end of every section we have a list of what are the things to look for. So on the people section, I'll read these from Matt. Matt wrote all of these. Matt, our CEO. On people section, " You woke up in the middle of the night convinced that you're the only person in the company who cares about your core values. That's a sign that you need a chief people officer." Or, " You're spending too much of your own time training managers and leaders or working on interpersonal dynamics for your leadership team. That is a sign you need a chief people officer." So I'd recommend looking at Startup CXO as a good reference for each of the different roles. It's more of a reference guide than something you want to read cover to cover, but there's some really good tips in there about that.

Holly Enneking: That's awesome. Great recommendation. Thanks Cathy. So Patti, thinking about this a little bit more, how can you go about effectively identifying the type of role you need to hire, and prioritizing the roles, and what that structure of your leadership teams would look like? How would you approach a big puzzle like that?

Patti Dorsey: Yeah, this really goes back to the leadership roadmap that Cathy just talked about. There are a lot of different ways to build your leadership team, and most companies don't have the luxury of filling all of those roles with full- time hires at the same time. So I'd recommend really first looking at the current team as mentioned earlier. Every role is likely being filled by someone on the current team. As you look through the team, ask yourself two questions: What's the most important for the business right now, and where are the biggest gaps right now? So maybe it's an area that someone's covering, but it's not really their core area of strength, or it takes up a lot of their time and energy, or maybe they just aren't doing enough of what the company needs at your stage of growth. So there's really not a one- size- fits- all answers, but again, going back to for instance, the people example that Cathy was just talking about. You'll want to prioritize this if the answers to those two questions that I just posed were... For instance, the question, " What's most important for the business right now?" Say you've hit product market fit and you know that you're going to have to hire a lot of people and scale quickly, so that probably means you might want to start thinking about hiring a chief people officer. Or the other question, " Where are the biggest gaps?" If you're finding that you're struggling to recruit or you're having retention issues, turnover, the culture isn't scaling effectively, those are also signs that maybe it's time to look at a chief people officer role.

Holly Enneking: Nice. I really like this idea that you sort of brought up already and maybe dig into it a little bit more around maybe you've got someone in a role and evaluating whether or not they're the right person to take you into another phase of growth. So for example, I'm a head of marketing. Am I ready to scale into a chief marketing officer role, for example? So Cathy, I'd love to hear your perspective on how you go about evaluating someone who's currently on the team in a role and then making a determination about whether or not they're the right person to take you into the next phase, and managing what could be a pretty delicate conversation and decision to have to make. Especially if there's existing relationship, sort of long- term involvement in the team, that can be a tough one to handle. I'd love to hear your point of view.

Cathy Hawley: Yeah, absolutely. So we have a matrix that we use. We used this when we wrote Startup CXO. We have every C- level role we have. We have what do we really think it takes to be successful in every stage of the company's growth? So I'm happy to share that with people if they are interested in looking at that, but that's a really good way to look at what should they be doing now in this stage of growth? What should they be doing in the future stage of growth? If you don't use that, use your own matrix of, say, I'm going to go back to chief people officer again, what do I think the chief people officer needs to be in three years? And then looking at what are the gaps between where the person is now and where we want them to be? You can do that by either doing a 360 with them where you get feedback from their team, yourself, themselves, their team, or just do a one- on- one performance review and look at where do I think they are and where do I think they need to be? Then the next part is really an open, transparent conversation about that, and that's the place I see a lot of CEOs getting stuck is not having that conversation, especially when like you say, " Holly, it's difficult. So maybe I'm going to tell you that I think there's a big gap between where you are now where I need you to be in six months and I don't know that you can fill it." That's a really hard conversation to have, and maybe I'm going to bring someone in above you, but the earlier you have that conversation and the more you're giving people the opportunity and the ramp to develop themselves and actually be ready for that role, the happier you're going to be and the happier your team's going to be. If you do come to a place where you say, " All right, let's talk it through and what I need for head of marketing, it's a pretty big gap to fill, but let's talk about it. Do you want to fill it? Are you motivated to fill it? If you're going to fill that gap and get the experience and the skills needed to do your role at the next level of the company's growth, then create a plan for doing that." Get them maybe it's a mentor, maybe it's some training, maybe it's experience outside. Sometimes it's even sitting on a board of a different type of company, but really be thoughtful about how do you get those skills in the period of time that you need to gain them? And then you can check in along the way. Are you making the right progress towards what you need? If someone isn't making the right progress and you're having those conversations, it's a lot easier conversation to say you're either not the right person for the role. You might self- select out or bring someone in above me because I don't really either want that role right now, or I need support in it, so bring someone in above me and then over time I'll get those skills and be able to do that role either here or somewhere else.

Holly Enneking: Yeah, I think that is a great point. It goes back to what you have both mentioned before as far as having that leadership roadmap. Having something like that where you have taken the time to sort of map out where you're going, where you need people to grow, makes it a lot easier to have that transparent conversation upfront so that no one is surprised. That's always the goal is you don't want anyone to be surprised by feedback or a decision that's made that potentially impacts their role, and having that roadmap is a great tool to help avoid some of that. Patti, one of the things that you mentioned earlier that I want to circle back to again is this idea of data and helping to use data. Obviously Cathy mentioned having the 360 reviews and some other things. What are some other data points that someone could use if they're evaluating a person who is currently in a role and whether or not they're the right person to move forward or if they need to be bringing someone else in?

Patti Dorsey: Yeah, and expanding on that, certainly like performance reviews, learning outcomes, turnover rates, retention rates, identifying really the high potential talent and setting up programs and strategies around that type of talent. What's coming out of exit interviews. A lot of times people leave people, so if you're looking at leaders, there might be some good data there to reflect upon. And also employee engagement surveys are never a bad idea. That should be done at least annually and maybe do quick pulses a couple of times a year as well. So there's so many types of data, but those are just a few examples.

Holly Enneking: That's great. I'd love to hear from both of your perspective, having worked at a lot of different companies, worked in a lot of hiring roles, when we're thinking about prioritizing roles and maybe where to make investments, what have you seen in the companies that you've worked with as far as they tend to have these types of roles on board and then add these as a phase two, maybe add other roles as a phase three? Is everyone starting with a chief marketing officer or is that a hire you make down the road? I'd love to hear if either of you have a perspective on maybe core people to start with and how you think about expanding a team. What's your baseline and where can you grow?

Patti Dorsey: You, Cathy? Or me?

Cathy Hawley: Sure.

Patti Dorsey: Okay, yeah. For me, I think it depends upon the priorities of the company first. So say you're developing a product, so you might focus more on your CPO, your chief product officer or chief technology officer and build out the engineering team. Then when it's time to go to market, you want to have someone with that strong skillset. It could be a marketing person, a sales person. What type of sales is it? Inbound sales, outbound sales? So I think it depends upon what stage the company is in and what their priorities are.

Cathy Hawley: I would agree with that, and I'd build on often companies like the founders are... Often you have a technical founder and maybe a CEO and a CTO so that's often a starting place. I think you always need to cover finance and you need to have... Most of the functions are at least covered, but we do see finance as one of the first roles, even if it's in a fractional space. Product is a little bit later sometimes. Sometimes the technology person also covers product. And then to Patti's point, it really just depends on the priorities of the business at that point. Growing really quickly and you really care about culture, you need to make sure you're covered on the people front. You're starting to go to market, you need to make sure you're covered on the marketing front, probably sooner rather than later. Or if you're going to market through partnerships instead you might have a partnerships person before you have marketing, but you probably need some go- to- market muscle early on, whether that's marketing, sales or partnerships.

Holly Enneking: Yeah. One thing we haven't touched on yet that I think you could probably bring some perspective to as well, Cathy, is when you advise someone to maybe go with a fractional hire over a full- time hire or vice versa. Knowing that there's this big boom in the fractional space of people using that as an alternative to the traditional full- time hire, are there certain considerations that you see that make you maybe advise someone one way or the other about what they might need for their team? And Patti, you're welcome to weigh in.

Cathy Hawley: Yeah, usually for me it's like talking to them about what the responsibilities of the role are and what they think they need to cover. And if it seems like it's not going to be a full- time job but you really need a more senior person, maybe you need a more strategic person in there because the finances are complicated or something, I would recommend starting with fractional. There's a lot of times that you can start fractional. I actually think every role can be started as a fractional role and really being thoughtful about what does the business need right now? You want to make sure you're not spending half a million dollars on a full- time CXO when your business doesn't really need that right now. What it needs is someone to do payroll and benefits and execute, and maybe it needs someone at a strategic level 20% of the time. I do think the businesses are getting more creative about how to stretch their money a little bit, but also get the skills they need because there's a lot of talent out there now who is interested in doing less traditional type of work. So the companies who are being really creative I think are just open to different approaches to that.

Holly Enneking: Patti, anything you want to add?

Patti Dorsey: No, that's exactly what I was going to say before you asked the question. We're seeing more and more companies taking the fractional route for sure. So that is always, I think, a good starting point. We're seeing a lot of it, and I think Cathy hit the nail on the head there.

Holly Enneking: Yeah, I think another thing that we've seen too, which is really interesting to me is people starting out in the fractional role and then transitioning into the full- time role. So they've got some time to maybe learn the business, develop a relationship, start checking the boxes of what was needed at the beginning, and then have the opportunity if stars align and it works out for both parties to then turn that into a full- time opportunity, which is another really interesting way of going about it as well. Patti, I'd love to get some insight from you. We've been talking a lot about thinking about the types of roles that you want to hire, when you want to hire them, how you're sort of thinking about the makeup and the long- term strategy of your team, but there's also a big logistics component to making a full- time hire and going out and opening a role, getting it filled, all of that. I'd love to hear your perspective about what a CEO or a head of people should be thinking about when it comes to the time commitment required to hiring a new executive.

Patti Dorsey: Okay. Yeah, the time commitment. So it's interesting. We just wrote, along with one of the other co- founders of Bolster, Jen, Jen and I just wrote a blog article about that. Maybe we could drop the link in the chat, or send it out after this webinar or what have you. But really the more prepared that the CEO is, the hiring executive or the chief people officer, whoever's running the search is, the more efficient the process will be for them. Searches can range for executive hire as long as nine months. I mean, it really can drag out, or it could be less than 60 days like a search that we just completed for one of our clients for a chief revenue officer role. In that case, the CEO was really leaned in, carved out the time, very engaged with us as well as with the candidates and set up regular meetings. So some of the things to think about are how much time will be spent with the intake call? So we usually like to set aside one to two calls, so that could be up to two hours, just really taking a deep dive into the company, where the company is, what their priorities are, what the vision is. And then taking a deep dive into the role itself, like what would success look like in that role? What are some of the priorities? So in terms of time expectations, there's a couple of hours there. And then going back to we set up the weekly meetings and those are just 15 to 30 minute touch points to talk about the candidates that are in progress. Do we need to do any calibration? Usually that's done on the front end anyway. How do we just hone in on the right candidates? And then they should expect to spend, and we're talking about the CEO alone, just 30 to 45 minutes on the initial interviews for each of those candidates. We'd like for them to see maybe 5 candidates, definitely no more than 10 because we'll be weeding them out as well. And then the rest of the interview process will involve other members of the executive team, and debriefs once a selection is made, and then final interviews, taking them out to dinner or at least spending a significant amount of time for that last round, one to two hours. So all in all, it could be anywhere from as short or as minimal as 15 to 20 hours to multiple hours depending upon how many candidates are in progress. But the goal again, is really planning upfront, putting in the work upfront to really plan what that's going to look like, establish some time commitments in terms of touch points, and just really stick to that timeline.

Holly Enneking: Yep. That's great. Anything you'd add to that, Cathy?

Cathy Hawley: I'd just add if you're looking for a fractional or more on- demand, it's a little less time- consuming and it's a little easier to make a decision because it is more short term, expected to be short term. So it doesn't feel like quite as big of a decision as hiring an executive on who you expect to be with you for the long term. And then I'd just reiterate what Patti just said, is the CEOs who are really engaged in the process make the process go faster, which is really good for candidates and for the CEO. I sometimes think people wait too long to hire someone, but I also think if you go too quickly and you don't actually have the bandwidth to do a search, then you're shortchanging yourself and your candidates.

Holly Enneking: Yeah, that's a great point about the candidate experience as well, not just for the... A process that drags on is a poor experience for the CEO and makes it really difficult, but also makes it really difficult for the candidates on the other side too.

Patti Dorsey: I'm glad you brought that up. That should definitely always be like a top priority. Yeah, the candidate experience.

Holly Enneking: Absolutely. So just as we're getting close to the end of our time here, I wanted to wrap up with one final question for both of you. As we are closing out on 2023, which is crazy to say already as far as I'm concerned, and starting to think about 2024, what is one thing that a CEO or a head of people can be doing right now so that they can be more proactive about their hiring strategy as they head into a new year?

Patti Dorsey: Yeah, I would say what they can do right now is look at the strategic plan for 2024. What type of talent will you need to meet next year's goals? For example, are you planning to launch a new service offering or maybe enhance or build out a new product? Or maybe you're doing some internal work or migrating to a new IT infrastructure. So based on that, determine what talent you'll need to get there. Do you need to invest in your engineering team, or bring in a new CTO or full- time CTO, or develop a new leader who's there already to take the team there? Earlier we used the example of the new go- to- market engine, so does that mean bringing a new CMO or develop the one that you have? Someone who has the chops to develop the strategy for that and can hire the right team to execute? And then think about the budget because budgets are real. So that other option is there that Cathy brought up earlier about the fractional hire. Do you really need a full- time C- level person over those critical areas or can you get it done with a fractional, or an interim leader, or even an advisor to the existing leader? All of those are what we refer to in the market as on- demand talent. So I would say those are just a few things to keep in mind and things that you can look at right now as we close out the year.

Cathy Hawley: Yeah, I don't have a lot to add to that. I'd say the same thing, is if you are kind of Q3 looking at your strategic plan and then your hiring plan for 2024, you could get ahead of the game and start recruiting in Q4. A lot of people do slow down their recruiting in November, December, but you don't have to. You could start and have somebody who starts middle of January and really helps you achieve those goals instead of having... If you need new people on the team, if you don't start hiring them till January they're probably not on board till March, so you're losing a quarter of productivity and runway towards your goals for the quarter, for the year. So yeah, that's what I would do. I would probably start the strategic planning process and have it finished by Q3 and have the hiring starting in Q4.

Holly Enneking: That's great.

Patti Dorsey: Yeah. As you mentioned, Cathy, people always say like, " Oh, there's not much hiring. No one hires over the holidays or towards the end of the year." And I have to say, in my experience as a recruiter for 20 years, that's really when we get the attention or can get the attention of candidates. They've slowed down, they're at home, they're answering emails, they are contemplating what their next year is going to look like, what are their goals? So it really is a good time to take advantage of that and strike the opportunity.

Holly Enneking: Awesome. Well, thank you both so much for everything that you shared today. So helpful. We will be sending out a link to this recording and we'll also make sure to include the links to the couple of resources that Cathy and Patti shared during this conversation. If you'd like, you can get access to more content from Bolster if you go to content. Bolster. com. We have all of our blogs, some other past webinars, our podcast as well, the Daily Bolster. If you're thinking about your team as you head into the end of this year into next year, you can get connected with our talent consultants, people like Cathy and Patti here just by signing up at Bolster. com. So we'll put those two links in here. But thank you for taking some time to join us today. We hope you found this valuable, and please feel free to send us any thoughts and feedback that you have as well. Or if you have questions that you'd like us to follow up on, we're happy to answer those too. Again, thank you Cathy and Patti, and thanks everyone for joining today. Have a great rest of your day.

Patti Dorsey: Thank you.

Cathy Hawley: Thanks Holly.

Holly Enneking: Bye.

Cathy Hawley: Bye.


Scaling your leadership team is a vital part of scaling your company. If you haven’t thought about your hiring strategy—or if you haven’t revisited your plan recently—now is a great time to do it. In this webinar, Bolster talent experts Cathy Hawley and Patti Dorsey discuss how leaders can know when to hire, what roles to hire for, and how to find the right talent. This virtual fireside chat includes insights from their real-life recruitment experiences and practical tips for scaling executive teams.