#14 JooBee's newsletter

TL;DR

😥 Exec struggling during onboarding? Check your 3Cs

👩🏻‍🎤 If I want a high performer, I need to be a high-performing manager

💥 Start-up career hacks with Dinye Hernanda (exclusive content)

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Question: I'm feeling uncertain about my new exec. They're just not grasping things the way I expected them to. I had hoped they would handle X, but they didn't. And when Y happened, I expected a different approach, but it didn't happen.

Shouldn't they know what to do without me having to spell it out?

Founder

Exec struggling during onboarding? Check your 3Cs

This is a classic - “Shouldn’t execs know what to do?” Yes…if you hired psychics🧐. Misalignment during onboarding happens more often than we'd like to admit. In a very similar scenario, when a CMO joined us, my founder wanted the CMO to "sort out marketing," which, to them, meant optimising processes and delivering clear reports as a priority. But for the CMO, it meant diving into a strategic analysis to ensure our marketing efforts were hitting the mark.

This misalignment became evident as the founder, simmering with discontent, opted to give the CMO more time by extending their probation to resolve issues, while the CMO was left working off assumptions about what the founder truly wanted. 

You can’t outsource alignment

Typically when execs join a start-up, the founders often outsource the onboarding of their execs to the HR leader, Chief of Staff or EA, and assuming the execs will figure it out. They’re experienced hires, right? But as we saw with the CMO, this assumption was precisely what led to the disconnect and misalignment.

As a founder, it's on you to ensure your execs are properly onboarded - you are after all their manager. While as an HR leader, I’d advocate for comprehensive support, I know firsthand that's not always feasible or practical. So,  the bare minimum requirement is to ensure the '3 C's' are met: clarity, connection, and confidence.

1️⃣ Clarity: past, present and future

Your execs will be part of the team making business decisions, and to make decisions that are effective for your company, they need to have a grasp of the past events (what happened), the present (current challenges and successes) and the future expectations (the destination the company aims to reach). 

If you're thinking that their peers, HR or your vlog can brief them on what happened - well, you're partly right. They can certainly provide information on what occurred or what needs to occur. However, what they can't offer is the underlying rationale behind those events - the "why" behind the decisions made, the factors considered and the beliefs driving certain actions. This is something that only you, as the founder, can provide with the most accuracy.

2️⃣ Connection: with you

One key to their success, though not the only one, is their ability to work effectively with you and vice versa.

Hiring an exec is like an arranged marriage.

You have the matchmaker (the search firm) who, based on your and their requirements on paper, arranges a few candidates for your review. You meet the candidates, and your family members (your current leaders) also meet them to gauge their suitability. Based on a few formal meetings, you propose marriage, and then they join your family. Now, imagine if you immediately decide to renovate a kitchen together or go on a family holiday - what are the chances you won't argue due to differences in opinions, style and taste?

So, once your exec "marries" into your company, you still need to establish connections and get to know each other - what is important to you, why it's important and vice versa. A higher frequency of communications early during onboarding is key to calibrating any misunderstandings and allowing both of you to adapt to each other’s expectations and working style. Ultimately, you need to be able to work with each other and prevent an early divorce due to "irreconcilable differences."

3️⃣ Confidence: because it is lonely at the top

Just like you, their role is lonely  – they’re the only CMO, CTO, CRO, etc., in the company. They also experience a sense of isolation in their roles, especially when facing early challenges during onboarding. If things aren't going well, they can't easily discuss it with their team (they're supposed to inspire them!), nor can they turn to their peers (for fear of being seen as unequal). If they can't talk to you either, self-doubt can snowball into full-blown imposter syndrome. Fear not, I'm not suggesting you become their therapist; you just need to be their manager. A short feedback loop during onboarding is crucial to either reaffirm or pivot your execs, and give them the confidence to navigate in the right direction of travel.

Your execs will figure it out, but you could accelerate the journey to performance

It's not a problem if you opt to outsource the onboarding of your execs and let them figure it out on their own. After all, they're experienced hires; they WILL figure it out without a doubt. 

But here's the thing to consider: what if they could figure it out in 3 months instead of 6, or 2 months instead of 4 with your support? Wouldn't you want to do everything you can to set them up to leverage their experience and make an impact on the business as soon as possible?

If I want a high performer, I need to be a high-performing manager

Early in my journey as a manager, I brought onboard an incredible People Partner with extensive experience from a larger enterprise. He hit the ground running and dived into key projects. I assumed all was well until I received feedback halfway through his probation.

Turns out, his approach was more aligned with the structures of large corporations. He prioritised addressing strategic challenges at a functional level but overlooked tactical issues. Although he was adept at fostering relationships with functional heads, he did not cultivate relationships with their direct reports. This practice, common in larger organisations, left middle managers feeling disconnected.

He gracefully took the feedback onboard and pivoted within a week - a testament to his adaptability. Everyone was amazed. Unfortunately, despite the turnaround, he decided to part ways before the end of his probation. It was a tough pill to swallow😔

High performers also need to be set up for success

I couldn't help but think, "What if I'd given him that support from the get-go?" Reflecting on that experience, I realised my mistakes:

Firstly, I didn't clarify and calibrate expectations well, including expectations from our stakeholders and our start-up’s environmental needs. Secondly, I assumed his experience meant I didn't need to spend much time with him, which was a big miss in building our connection. And finally, I didn't adequately support his transition into our start-up culture, which is a significant adjustment for anyone.  

Bringing someone with corporate training adds a lot of value - they have solid foundations in their expertise. I recall how strategically my People Partner managed the entire performance review process. 

Now, when I bring someone new on board, I make sure to nail the 3Cs

The effort invested during this time is directly proportional, if not more, to setting the tone for their performance for the rest of their career on my team.

👓Clarity: you cannot overemphasise this

Before their first day, I ensure they receive their OKRs or goals. During their first week, I'll give them a rundown of what works, what doesn't and the nitty-gritty of our culture. I also share insights into my thoughts, quirks, triggers and fears, while learning about theirs. 

Most importantly, I clarify the 'why' behind our priorities and decisions. If I can't explain, my team can opt-out. They might not like the ‘why,’ but they will always know the rationale behind my decisions.

🗨️Connection: touchpoints accelerate relationship-building

I used to do weekly 121s with new team members. But one of my direct reports showed me the power of frequent touchpoints by setting up 3 x 15 mins 121 meetings with me each week when she started (high performers, they’re proactive!😅). It kept us aligned and clarified any questions she had as a newbie. And guess what? She nailed a crucial project in her first month!

Now, I ensure to have at least 2 to 3 meetings a week throughout probation. My direct reports lead teams of 5 to 20 people, supporting either a department (50 - 100 people) or the whole business (200-400 people). Setting my direct up for success is crucial - for their team and our business overall.

First 121 template

During the first week of onboarding, my very first 121 is all about getting to know each other faster. Here are some examples of questions I always make sure to cover.

🪴Confidence: shapes long-term performance

During his probation, my Director of Talent called me about a significant mistake his team made. He not only fixed it but also figured out why it happened and took steps to prevent it from repeating. I thanked him sincerely for keeping me informed and asked if he needed anything else.

He was like, "That's it?😲" And I was like, "Yup 😄."

I could tell he was surprised and relieved when we talked more. He thought I'd be way tougher, especially with other mess-ups that week. Since then, he's been upfront about any issues and disagreements. I strongly believe that the tone we set during probation shapes how our team members perform confidently in their roles.

Top talent looks for top managers

My experience taught me a valuable lesson about assumptions. We often assume that high performers will naturally figure things out. While they can pivot quickly, as my People Partner did with feedback, I learned the hard way; if you fail to support them adequately, it's challenging to regain their trust, and they may choose to leave. So, if I want to attract top talent, I need to step up as a high-performing manager myself.

What do you think❓

Who typically assumes the responsibilities of onboarding execs in your start-up?

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Seek external mentors: your manager might not be from your field 

Sr. Learning & Development Manager
HeyJob

“I was flying solo in a way I never had before.

The mistake I made

Transitioning to a start-up from the corporate world, I was all set to head the Learning and Development (L&D) area. What I didn't see coming was the lack of a support system that I was used to. My manager, though adept in general project management, lacked a background in HR or L&D and wasn't equipped to mentor me. With the expectation to show up as THE L&D expert, the pressure was on, and doubts about whether I was up to the task began to creep in. I was flying solo in a way I never had before and I underestimated how much I'd miss bouncing ideas off colleagues who understood my work.

The one thing I wish I knew to avoid that mistake

I wish I had recognised the importance of seeking external networks sooner. In the start-up environment, where managers often lack specialised expertise and finding peers in similar roles can be a rarity, tapping into a broader professional community becomes priceless. Joining groups like L&D Shakers and Offbeat opened my eyes to a vibrant world of professionals eager to engage, share experiences, and offer mutual support. Regular dialogues with L&D leaders from other start-ups have been a lifeline, rescuing me from many moments of isolation and the paralysing over-analysis.

One tip to hack your career in start-ups

Cultivate a professional network beyond your company. To supplement the guidance you might be missing, actively seek out an external mentor who can provide the specialised direction you need. Additionally, don't stop at attending networking events; go a step further. Whether it's a coffee catch-up or a quick Zoom call, exchanging with peers outside your bubble can be a game-changer to your practice and enrich your perspective. Connect with those on a similar journey and commit to regular peer learning group sessions where you can brainstorm and work on projects together.

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