The TroopHR Podcast

Ep 33. Rethinking the First 90 Days: A Startup Playbook with Cindy Gordon, Chief People Officer, Madison Energy Infrastructure

• Season 2 • Episode 33

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What does successful onboarding really look like in a startup? In this candid and strategy-packed episode, TroopHR host Taylor Bradley sits down with Cindy Gordon, a seasoned Chief People Officer, to reframe how people leaders should approach their first 90 days—especially in high-growth, fast-paced environments.

Cindy shares invaluable insights drawn from her own recent experience stepping into a new executive role, emphasizing why the traditional “listening tour” might not cut it when speed and impact are paramount. She unpacks the realities of being brought in to "fix something," the importance of quick wins to build trust, and how to thoughtfully navigate existing team dynamics and executive expectations. From handling that first spicy AMA question at all-hands to identifying the organization’s “shadow org,” this episode is a must-listen for HR leaders seeking to thrive in their early days.

For more insights and to join our community of forward-thinking HR leaders, visit troophr.com. Don’t forget to subscribe, rate, and share the show.

Credits
TroopHR Founder: Tracy Avin
Show Producer: Nicole Fealey
Show Host: Taylor Bradley
Note: Transcripts generated by AI.

Ep 33. Rethinking the First 90 Days- A Startup Playbook for New People Leaders with Cindy Gordon_V.1 

[00:00:00] Cindy Gordon: If people are coming to you and asking you where you are at in progress on certain initiatives or what you're doing, then you're not communicating enough.

[00:00:15] Taylor Bradley: Welcome to the Troop HR podcast. I'm your host, Taylor Bradley. Today's episode is one I've personally been looking forward to. Because we're digging into a topic that is top of mind for so many HR leaders, especially those stepping into new roles. I'm joined by the incredible Cindy Gordon, a seasoned chief people officer with a track record of building impact quickly in startup environments.

[00:00:42] Taylor Bradley: We're talking about the first 90 days and what it really looks like when stepping into a role as a people leader inside an organization. And spoiler alert. It's not all listening tours and onboarding checklists. Sydnee brings the real talk, [00:01:00] the strategy, and some seriously thoughtful insights into how to balance speed, trust, and long-term impact.

[00:01:09] Taylor Bradley: But we begin on the ground floor by first asking, what does high quality onboarding look like? 

[00:01:18] Cindy Gordon: High quality onboarding is. Where a new hire, and this could be for any level at a company, any function where you have joined the company and from day one, you're given access to information to help you ramp up quickly in your role.

[00:01:37] Cindy Gordon: And you understand how all of the pieces of the organization work together. And you may have a, get an understanding of how they don't. And depending on your role, you may be brought in to help build some of that or. Right size something or build operational efficiencies, but you're starting to collect all of that info, and the hope is that onboarding actually starts when [00:02:00] you're interviewing.

[00:02:00] Cindy Gordon: So you start to get a sense of what it's like to work at a company and you're collecting info, both the stuff that is outwardly and intentionally shared with you during that selling process, but also all of the unspoken stuff that you're starting to pick up on. 

[00:02:17] Taylor Bradley: Yes, that recruiting process can certainly be helpful.

[00:02:21] Taylor Bradley: One thing that I have used in my career is at that stage, almost the anti sell that you give at some point to your final candidate, so they get a real crisp view of what they're walking into before we get into, I like that, the dog boarding piece. Hey, have you used things like that in the recruiting phase too?

[00:02:40] Cindy Gordon: I don't know about the anti cell. I do craft questions. That serve dual roles where we're connecting dots on the backend around motivations and drivers to see if they're aligned with the company's values, and then outwardly facing it is [00:03:00] a showcase of. Our investment in somebody's professional development and coaching and helping them understand what the company's values are.

[00:03:07] Cindy Gordon: So there's a bit of a, an art and science psychological component to questions, but I really like the idea of the anti cell that's very like direct and cuts to the point, and I think that could be really useful. I'm going to take note of that actually. I'm gonna write that down. 

[00:03:24] Taylor Bradley: Now. I've experienced this, you've experienced this several times.

[00:03:30] Taylor Bradley: Is we arrive on day one, so let's just start there. First, 24 hours on the job, how would you recommend executive leaders and chief people officers approach that first 24 hours? 

[00:03:44] Cindy Gordon: There are a number of ways I've seen some of my peers come in having fully build out their roadmap, and maybe they've already collected enough info during the interview process to do so, but I like to have some mindset.[00:04:00] 

[00:04:00] Cindy Gordon: Phrases in mind to keep me focused because it's so easy when you jump right in to be excited about the work that you're going to be doing and you wanna do it all. And one mindset shift for me is startups don't really give you that 90 days, right? That's usually a construct that we've thought of as people, professionals, to help set people up for success and to enable our managers and leaders to think about that.

[00:04:26] Cindy Gordon: But for us. We're stepping into something that we're expected to build. And so you're not given the 90 days from the outset. You need to move fast, you need to move strategically, and it's, you know, we were debriefing on this before, but. The whole idea of coming in and wearing your consulting hat and just observing and listening and learning isn't really real, especially if we're speaking on the context of startups.

[00:04:51] Cindy Gordon: You're walking into a system that's already in motion and there are expectations in place. There's usually a reason why people, professionals are brought into a role. It's not like, [00:05:00] Hey, it's dreamy. We, we need, we know we'll need a a people person one day. It's usually something's broken and it signals, Hey, we need this.

[00:05:09] Cindy Gordon: So. Speed is survival in startups. And I think I will be speaking in the context of that primarily because of my past operating roles. You're brought in because something's broken and founders usually want something that they want quick traction, and so all of the patients and intolerance levels are tied to board and investor pressures that they're getting.

[00:05:33] Cindy Gordon: And so you have to act quickly and I, I read this. STA and a workplace survey that if you can have a quick win as a leader within your first 45 days of starting, you are going to be rated higher impact in your first year of your job by a factor of like two times than [00:06:00] if you don't do something that offers a big win within that first.

[00:06:04] Cindy Gordon: 45 days. So there's a little bit of pressure that we should put on ourselves as new hires or as execs stepping into a role to have a quick win. I think what that looks like could vary by what set of founders thinks is a quick win versus what you might think is a quick win or what the organization will think as one.

[00:06:25] Cindy Gordon: One example of this is I've just stepped into a new, I'm six weeks in, so this is very fresh on my mind, but. We are thinking about how we're working remote. We've got a remote workforce and we're hybrid and distributed, and there's a push as we're seeing at a lot of companies to be back in office. And so I think a big quick win for the executive team is to get everybody back into the office.

[00:06:53] Cindy Gordon: Cool. And if I, if that was my first initiative that I'm rolling out. I'm not going to be getting much trust from the [00:07:00] organization because I don't think everyone, and I know this to be true, is on board with that. And so when I think about a quick win, it might be different than what the executive team has in mind, and it's a matter of balancing that.

[00:07:13] Cindy Gordon: But you do have to have something that starts to build the trust of the organization. We could be. Scary people coming in. Executives can be scary. People coming in and you need something that starts to build trust before you start rolling out a bunch of other things. They're still critical to the business.

[00:07:30] Taylor Bradley: It seems. Every time I start a role, what I typically will hear is, Hey, we've been putting off handling this really gnarly employee relations case until you got here. Here you go. But it's a great way to build trust and I've heard some folks. Say, I wanna take the listening tour and those things, I think that can happen in parallel, but for the listeners to reiterate, getting that immediate win under your belt isn't politics.

[00:07:59] Taylor Bradley: It's [00:08:00] building credibility. Mm-hmm. Building trust for you to implement your vision for the role. The other aspect when coming into an A new role is building that trust and credibility with your immediate team or your indirect reports. What are some of the avenues that you would recommend to do that as well as the organization, but focusing on the team first?

[00:08:24] Cindy Gordon: Yeah, and that can be tricky if you're inheriting a team and figuring out the dynamics there. And that has happened in all of my chief people officer roles. I think one, you need to understand where somebody is at and you don't, I, in my opinion, don't wanna make really big sweeping changes. Straight from the outset, there is likely a misunderstanding or, or there isn't as much of a light shining down on what the people [00:09:00] function does strategically as a business function for a company.

[00:09:05] Cindy Gordon: And it's likely that you're coming in as an executive to start to shine a light on that, and you need to. Understand all that the team is that has been working so hard to build it up to where it is now, what they've done, and I think that's really important. I think a lot of companies and founders bring in a very junior set of people or that one.

[00:09:30] Cindy Gordon: Person who might have started out as a recruiter or even a junior recruiter. And then they're expected to take on all of the responsibilities for the people work, and then they're like, oh, they didn't meet the needs and now we need to hire over them. And I think that's part of the misunderstanding of what it is that we do.

[00:09:47] Cindy Gordon: And it's on us as executives to make sure that we're helping to showcase what thinking strategically looks like in running a people function. And it's usually. [00:10:00] Most of what I've seen is sharing more of the why behind what it is that we do, and that we do have to educate people. I look at every opportunity I.

[00:10:12] Cindy Gordon: Where it's mis, there's misalignment where we're expected to do transaction oriented work or we're getting asked a bunch of questions and we're on our heels because we're in a reactive state as a learning opportunity. Or if we get a question around something sticky, I don't know, like give, tell me what you're.

[00:10:32] Cindy Gordon: Wage gap analysis is, and why aren't we paying people fairly? If we get a question like that from the employee population, then I like to look at that as, okay, we don't need to get defensive. Let's use this as an opportunity. We've got the ears of people to educate them on what a wage gap analysis actually looks like.

[00:10:53] Cindy Gordon: So, and I, I find we're constantly playing defense and. Coming in as an [00:11:00] executive, you can help to shift how junior people teams are thinking about things. 'cause they're just ramping up and trying to build subject matter expertise. I also think another thing for people, professionals is I, as a chief people officer, don't want to be the subject matter expert on everything.

[00:11:18] Cindy Gordon: And I wanna create that space and runway for team members to get smart on things and teach me something out there by benchmarking, by getting connected to peers and other other companies. And so I think that's really important to see. Where they need to grow and then encourage them and connect them and find, hear those blockers for them, and coming back with subject matter expertise to allow you to learn even more.

[00:11:49] Cindy Gordon: And not just jumping in with, because you know everything. There may be times though where you do need to see somebody out, but I think you need to give it a little bit of time if [00:12:00] you can. To see where they need to ramp up. And is it just a simple case of, oh, they've never had somebody who's been focused solely on this function and can help them clear blockers and see things differently.

[00:12:12] Cindy Gordon: So giving people the space and runway, if you can, is super helpful. 

[00:12:16] Taylor Bradley: That person that went from an emerging talent role to the head of people of a very small startup in a matter of years, keeping them around, uh, what you mentioned, uh, that institutional knowledge they have. Can be invaluable for the transition period or the ramp up of you, right?

[00:12:36] Taylor Bradley: While you're bringing in the expertise, they have some inside baseball knowledge that's really helpful. The other aspect that we touched on briefly is now that we've started to build rapport with the team, one of the other meetings that we'll probably have to attend in the first few weeks is the executive leadership team meeting.[00:13:00] 

[00:13:00] Taylor Bradley: And whether that's weekly or however the cadence is that first meeting heading into that, what are you prepared for 

[00:13:07] Cindy Gordon: when you were asking that question? A whole bunch of. His historical moments have popped into my mind. So the first day of the last three chief people officer roles that I stepped into, I just recall being handed a list with a litany of things on it that I need, that they wanted me to focus on.

[00:13:27] Cindy Gordon: A lot of them were eager to hand things off because they were cobbling together some semblance of a chief people officer amongst the executive team, and they're just like, okay, now we can hand it over and we're done. And they're gonna do all the work. And so I think coming in to that meeting, listening to them, I also think they're shouldering a lot.

[00:13:48] Cindy Gordon: And a lot of them, admittedly, most of them admittedly, are relieved that somebody's joining and they want somebody to come in and help clean things up. [00:14:00] I, I do think it is important to listen and to take everything in and not act immediately. Again, keep in mind that one like win that high impact win. It doesn't have to be a broad sweeping, like over engineered project.

[00:14:18] Cindy Gordon: What is that one small win that's going to build trust with the org? Okay, you can do that, but with the executive team. Fix less than you see going on right now. They might be sending you everything and being the eyes for you. You need to take some time to understand what the the shadow org. Is that exist, not what they're telling you from their vantage point.

[00:14:40] Cindy Gordon: And then you wanna prioritize that trust over doing everything immediately straight out of the gate. And that might look different for different po pockets of the org. What the senior leaders one might be really hyperfocused on growing their team. You're going to want to sit down with them. And understand their needs on [00:15:00] the hiring side and helping to clear blockers for them.

[00:15:02] Cindy Gordon: There another might have that sticky employee relations issue and they might have put somebody on a PIP and then they never really. Followed a structured PIP process or they put them on a PIP and they shouldn't have, right. And they should have just said goodbye to them, and you'll help them navigate that.

[00:15:18] Cindy Gordon: But I do think there's more of this bespoke process in building trust with each of the execs and understanding where they're at in their capabilities and needs on the people side, and figuring out how you can clear blockers for them. If you can clear blockers for people. Maybe that's the theme here, whether that's for your direct team that you're inheriting.

[00:15:37] Cindy Gordon: And or for the exec team that you're partnering with. I think that can go a long way, but that's where I think it's really important to listen and create more of the bespoke approach than thinking, okay, I have to do everything that everybody's asking. Take it all in, and then figure out where you're prioritizing things.

[00:15:54] Cindy Gordon: But the biggest prioritize priority there is trust over actioning on things [00:16:00] immediately. We will burn ourselves out if we try to do everything immediately. That's not sustainable. It's not actually impactful. 

[00:16:08] Taylor Bradley: It it, what kept running through my head as you were walking through these examples was having a sense or coming to the table with a sense of curiosity that can be turned into action is getting to know the business.

[00:16:22] Taylor Bradley: You hit on one tactical point that not in the ordinary management books is understand the shadow org and double click on. When people say, Hey, I would like these three things for you to do, they may actually be very clear on what those three things are, but what are the symptoms behind? Yeah. Them getting to the point.

[00:16:44] Taylor Bradley: And one thing that you said that I can never imagine happening and is a manager mishandling a pip, I, you know, I've just never seen that in my career. 

[00:16:52] Cindy Gordon: So it's an anomaly. An anomaly, sorry. 

[00:16:55] Taylor Bradley: That's one of those three deviation moves that we gotta watch out for. Right. The, the other thing that came up [00:17:00] too is.

[00:17:03] Taylor Bradley: The, one of the other big meetings that we attend as executives, especially when you're new in the role, is the first all hands. And in particular, if it's an environment where it's an a MA style, we tend to get spicy questions as being ahead of people coming in. What advice would you have for that? 

[00:17:22] Cindy Gordon: I, so I believe.

[00:17:26] Cindy Gordon: That we need a multi-channel approach to communicating and fielding questions or for people sharing their thoughts. And in the realm of psychological safety, you don't know how comfortable people are in certain forms, so some aren't comfortable going directly to their managers. They're not comfortable going directly to a founder.

[00:17:49] Cindy Gordon: So you do need to create a channel that is somewhat. Anonymous or open and public for people to feel like they are heard, and so you're not breaking down trust. [00:18:00] We do need to offer those opportunities for people to surface things because those conversations are happening anyway, and I'd rather know those spicy questions than not know them because they're, they're anyway.

[00:18:12] Cindy Gordon: At least people are comfortable surfacing them. But to get ahead of that, I would come up with an anonymous all hands question form that people, where people submit questions, it is owned by, I would say the people team. And then we take those questions in advance. We close that form the day before at a certain time so we can then.

[00:18:35] Cindy Gordon: Read through the questions, figure out how we want to respond to them or find the right stakeholders who can appropriately respond to them, and then we address it. Sometimes the question is worthy of full all hands content that the CEO can then present on, right? Sometimes it's a quick answer to a question and we're starting to glean data that.

[00:18:54] Cindy Gordon: We need to add something to the company intranet so people have access to when benefits open enrollment is or [00:19:00] something, and then they're like the quick one-off questions where it's a great opportunity for a stakeholder to speak to a topic and give more, I dunno, like public exposure to. To what it is that the topic that is coming through for those sticky questions.

[00:19:16] Cindy Gordon: It could be that there is a mass exodus of people at the company and people are wondering what's happening. And at the end of the day, we need to then seize that as a learning opportunity and say, oh, they're worried about psychological and job safety, and if they're next, most people are always thinking about, how does this impact me?

[00:19:33] Cindy Gordon: And so then that's a great opportunity to address something and to learn from that as an executive team on how to handle. Departures, for example. So I, but I like control getting ahead of the narrative a bit by fielding questions up front, but still leaving that anonymous channel open. 

[00:19:52] Taylor Bradley: I actually like spicy questions to, to piggyback on what you're saying, because it shows that there's a level of trust in the organization where [00:20:00] someone may feel willing to share that opinion, right?

[00:20:03] Taylor Bradley: As opposed to it simmering under the surface. So hot takes welcome is generally what I say. Looking back, let's say you're 30 or 45 days in, what's one way that you would recommend new executives to take account of? Are they on track? Do they feel like they're trending in the right direction? 

[00:20:26] Cindy Gordon: My gut reaction to that question is, are you being asked a bunch of questions and.

[00:20:36] Cindy Gordon: Having to follow up on where you're at on things. If people are coming to you and asking you where you are at in progress on certain initiatives or what you're doing, then you're not communicating enough. And if it is not a matter of communication and you actually haven't started on things, then. You might be overwhelmed, and then that's where you should [00:21:00] tap in your personal board of advise of advisors, maybe the troop HR community to help you course correct and get out of the overwhelm.

[00:21:10] Cindy Gordon: It's a very lonely role, and I am certain that everything is being thrown at you in different directions, but you're not alone. We, we don't have to reinvent the wheel here. We're not starting from scratch. We have the community to leverage and I would say tap in others. If you find yourself in a place where you don't even know where to begin, 

[00:21:32] Taylor Bradley: there are so many times where I've turned to the true vi R community.

[00:21:35] Taylor Bradley: And you can put the wildest question in there about some of the most esoteric stuff, and there'll be someone, there'll be someone that, yeah, I went through that last week. Yep, no problems. Bye. So it, it's such a, it's such a great community for those types of questions. So the final one for you, it relax, not a spicy one.

[00:21:55] Taylor Bradley: We're not in the a MA right now is if people wanna get connected [00:22:00] with you, what would be the best way to do that? 

[00:22:02] Cindy Gordon: I would say, you can email me, uh, Cindy andGordon@gmail.com or find me on LinkedIn. You can connect with me on LinkedIn, but I would suggest emailing me directly if you need to set up time. I am not as in my LinkedIn inbox and as I should be because I get spammed all the time.

[00:22:21] Taylor Bradley: I have written down so many things that I'm actually gonna chair in my management meeting here in a couple hours with my team, so I learned a lot. Thank you so much for being on the podcast today. Thank 

[00:22:33] Cindy Gordon: you for having me. It was great chatting with you. 

[00:22:35] Taylor Bradley: Thank you for listening to this episode of the Troop HR podcast.

[00:22:39] Taylor Bradley: If you've enjoyed this episode, we encourage you to subscribe and leave a five star rating. If you would like to learn more about our community, please visit tro hr.com. In the meantime, keep living the dream.