The Toughest Transition: Peer to Boss

Meet the friends

This is the story of four in-house lawyers, all entirely fictional, but who may nevertheless resemble colleagues you might meet at the ACC Annual Meeting. In fact, our fictional four lawyers first met each other at that conference a few years ago. Myron and Dolly’s company, Status Quo, Inc. (SQI), is a traditional company run by a CEO with an authoritative style and a revolving door of general counsel. On the other hand, Greta and Edward work for Creative Culture Company (CCC), known by employees and customers for its creative and engaged culture.

About two years ago, both companies hired new GCs. From there, their paths diverged.

CCC implemented the succession management plan it’s had in place for some time, promoting one of the attorneys it had groomed for the opportunity.

SQI, while also hiring from within, first conducted an extensive external search. The company didn’t land its first choice, a widely known fact, including by staff attorneys.

While all four attorneys — Myron, Dolly, Greta, and Edward — are friends and have been for some time, they each took very different paths to their current positions.

Myron and Dolly

Myron and Dolly bonded in college over freshman math. They attended lots of college parties and partied on spring breaks together. They thought they’d be friends forever. But as life often goes, once the graduation ceremony was over, their lives and career paths went in separate directions.

Dolly went to work right out of college for XYZ Company and Myron went to law school. After a couple of years, Dolly realized she wasn’t making the difference or money she envisioned and decided to become a lawyer. She was lucky enough at the time to be working for a company that provided graduate school tuition reimbursement, and she admired the in-house counsel with whom she’d worked.

Meanwhile, Myron, now a distant friend, was a second-year associate at a downtown law firm. However, he wasn’t happy with his career or the number of hours he needed to work to be recognized, which resulted in a lack of work-life balance. After a chance conversation with Dolly, Myron learned about available opportunities at XYZ. He applied and joined the legal team.

Once Dolly completed law school and passed the bar, she also joined XYZ’s legal team and the two of them picked up their friendship right where it left off in college. Now they share family meals, vacations, and often bond over the work they’re doing. They’re both happy with the directions of their careers, and discuss their plans for growth and desires for professional promotions. About five years ago, XYZ was acquired by SQ Inc. and the culture began to change. For the first year or so things were still relatively good, even though they’d gotten a new CEO and general counsel after the acquisition. Their new boss was firm and fair, but distant and not nearly as hands on with staff as their prior GC. Both Dolly and Myron felt there was bias in favor of SQ Inc. counsel, but weren’t sure if that was the case, or if their new boss just hadn’t gotten to know and trust the XYZ attorneys yet.

Around the middle of the second year after the acquisition, the CEO and GC decided the legal staff was too large and a reduction in force was appropriate. They sought volunteers to accept voluntary separation and a severance package. While a few accepted, there were not enough to reduce the department to the desired size. At that point stress started to seep in, straining relationships as everyone felt their job was on the line. Not only was there tension between Dolly and Myron, but between the other attorneys as well. The strain between Dolly and Myron was simply a harbinger of things to come.

Then it happened. Their boss announced her retirement and the opportunity for someone in the department to replace her. Dolly and Myron both decided to pursue the opportunity and reaffirmed for each other that it would be OK no matter who got the job.

Greta and Edward

Greta and Edward’s career paths were a little more direct. They met as first-year associates at CCC and for the most part enjoyed working there. They had a great and caring general counsel who took lots of time with staff attorneys despite having a large legal staff. He was willing to invest in his counsel but was demanding when it came to a return on his investment. Staff respected him and rarely complained, even when occasional overtime work was required.

The company was innovative and collaborative, investing in staff resources like legal and soft skill training and coaching and mentoring. The GC was communicative and encouraged the attorneys to work in pairs or teams so that work was always covered, and they would have the freedom to avail themselves of not only training and growth opportunities, but enjoying their vacations without worrying about coverage and legal matters falling through the cracks.

The succession management plan identified attorneys able to be considered for promotion after achieving certain tenure and team management milestones. CCC didn’t promise attorneys that promotion would come from within, but the last four GCs were all elevated from the ranks, so it was important to position oneself for consideration for leading teams if being GC was a goal.

Catching up at the 2019 ACC Annual Meeting

Prior to SQI’s acquisition of XYZ, old friendships were rekindled and new ones emerged as Edward, Dolly, Greta, and Myron all attended the ACC’s

Annual Meeting. Edward and Myron were also friends from college, though not at the same school, and ran into each other at a reception. They decided to meet for dinner and invited Dolly and Greta to join them.

The foursome had a great time that evening talking about their individual challenges as in-house counsel and the joys they had in their respective roles.

Dolly shared her challenges of feeling she is behind others at SQI because she went to law school after beginning her career outside of the legal function. At the same time, having worked for the company prior to joining legal, she felt she understood SQI’s business in a way no one else in her department did, and thinks when the time comes it will give her a leg up in getting a promotion.

Myron, who works alongside Dolly, felt that his experience in a law firm would be an asset for him as well, though he wasn’t sure he wanted to be general counsel because of the pressures of being ultimately responsible for the legal services and staff to an entire organization.

Edward shared his desire to someday be general counsel, though he knew it was a longshot at his current company because he had yet to be identified as one of the attorneys in the succession plan. While he’d been at the company long enough, he hadn’t led a cross-functional or virtual team on a legal project and until that happened counsel were not automatically considered for promotion.

Greta, on the other hand, was a serious candidate for consideration. She had not only led two cross-functional teams, but had also taken advantage of the coaching and training made available by CCC since she passed probation. Greta wasn’t sure she wanted to be general counsel, but she made the decision to position herself as best as possible in case she decided she was interested. She loved the flexibility of being a leader or just one of the team when it suited her.

Over time, in addition to these conversations about being prepared and desire, they also discussed what would happen if one of them was selected over the other for promotion. Unfortunately, no one really thought there would be a problem and they generally skirted the issue.

The 2021 Annual Meeting

A few months after the 2018 Annual Meeting, Myron heard the news: He got the GC job. He immediately changed his behavior, forgoing the long lunches he used to have with Dolly.

Dolly, after the disappointment of losing the GC job, was doubly upset at Myron’s brusque behavior. She eagerly awaited the following year’s Annual Meeting where she could catch up with other in-house colleagues and network for a new job.

Over at CCC, Greta accepted the general counsel position and immediately reassured Edward that their friendship would not affect her treatment of him as an employee. They both looked forward to the next Annual Meeting to catch up with their in-house friends.

Coaching is a good thing

At the 2021 Annual Meeting, as a new GC, Greta signed up for ongoing additional coaching through the ACC to talk through some of the specific issues she’s been having in her GC role. Greta mentioned struggling with how to delegate assignments. Her legal department, despite being large, doesn’t have specialists — every attorney is expected to perform all legal services needed, as assigned. Attorneys have their preferred functions, and department heads have their favorite attorneys.

Greta often delegated everyone their favorite work, but there were times when it simply wasn’t possible. This was her Achilles heel. She felt guilty giving people work they didn’t really want and therefore aren’t adept at it. As frequently as she and her team discussed this problem and sought different approaches to address it, the problem persisted.

“If you have attempted to address this and continuously reach out to your team for solutions, why does this cause you such angst?” her coach asked.

Greta replied sullenly, “I’m not sure.

I feel like I’m doing a pretty good job managing the team and their feedback overall is positive, but there are these moments when I hand out assignments that I feel I could do better. Then I’m wracked with guilt for not doing better.”

The coach followed up with, “It’s not uncommon to feel like you should be doing better. In fact, that is a positive human trait. However, if you are doing the best you can, there is no need for guilt. If you are not doing the best you can, step up your game and do better. The only scenario in which guilt is appropriate is when you are doing nothing and have no plans to do anything. When you stop and think about it, choosing to do nothing is a choice. If you are doing something, guilt is a wasted emotion.”

“You’re right I guess,” Greta responded. “Maybe it’s that I don’t feel I’ve exhausted all possibilities. So, I will continue to think creatively on the matter and ask the team for any additional ideas they may have. Thank you!”

Nothing wrong with getting help

Generally, after her coaching sessions, Greta would schedule lunch with Myron to talk over newfound insights. They met frequently for lunch since their promotions. There is a sense of camaraderie between them since they are friends, but also relatively new to their GC roles. Greta has the benefit of a supportive company and CEO, along with the resources of her coaches. Myron, on the other hand, has been pretty much left to his own devices, as well as whatever insight he can gain from Greta.

At one particular lunch, Greta shared her feelings of guilt about assigning work, and her coach’s advice that she let go of the guilt. Myron agreed, but for a totally different reason.

Myron’s approach was that he and Greta were in charge and therefore, whatever they said goes. It doesn’t matter whether the attorneys agree, like it, or not. Greta asked him how that was working for him. He had to be honest and admitted that the approach wasn’t really working. He was having problems with Dolly and several others had left SQI for other positions. His department was short staffed, and everyone was overworked and grumbling. But he just assumed it was part of the price one paid for being the boss.

Appearance of favoritism with other attorneys

Myron went on to say that some of his attorneys feel that he plays favorites with Dolly, while Dolly feels like he is in fact harsher on her in order to prove he wasn’t being biased.

Greta often delegated everyone their favorite work, but there were times when it simply wasn’t possible. This was her Achilles heel. She felt guilty giving people work they didn’t really want, and therefore she isn’t adept at it.

Greta shared that she’d not had this problem. She explained that as part of her transition to GC, she made a point to sit down with her staff, both individually and collectively, at the very start of her role. She went on to express that while it was human nature to favor those you like, when those feelings can create a bias, intentional effort is required. Without addressing favoritism — whether it will play out amongst the team or not — the appearance will always exist. People can tend to think someone else is getting preferential treatment, even if it can be objectively proven that treatment is equal across the board. The only way to deal with it is through open communication.

As they talked through how he might better address the situation, Greta told Myron that he needed to gather his staff to air out all the unspoken expectations and problems bubbling under the surface. Until Myron did that, he was going to continue to have problems and lose staff.

Building trust in new role

One of the things new bosses have to do with their staff is to establish trust in their new roles, which still applies to friends. This is something that will take time, but again with proactive communication about the potential problems and a commitment to dealing with things as they come up, they can get there.

The best way to build trust in the new situation is to forget what you know about the prior behavior. Of course, this is easier said than done, but it is the best approach — otherwise both parties will use what they know to justify current behavior and treatment.

As Myron and Greta continued talking over lunch, Myron mentioned that he was having trouble trusting Dolly because he knew she used to take long lunches — often with Myron pre-promotion. While he told Greta that he had stopped taking long lunches, and knew he needed to give Dolly the benefit of the doubt, he was struggling to do so.

Greta reminded him that Dolly no doubt remembers his pre-promotion behaviors too, and is probably thinking what a slacker she has as a boss. “I know trusting your staff is a challenge Myron, so maybe working with a coach will help you to work through your blocks and gain some tools that will help you move forward,” offered Greta. Myron agreed and said that while he wanted a coach, SCI wasn’t willing to make the investment. Greta reminded him that this was his career and his staff, and it was his responsibility to intentionally become the best boss possible.

Managing disappointment

Myron and Greta were not the only ones having lunch at the Annual Meeting. Edward and Dolly, on the other end of the promotions, also found themselves talking about how things have changed.

It doesn’t matter whether it is winning little league MVP or an executive promotion; for most people, there are going to be hard feelings about not getting something they wanted. It may be lessened because you really care for your friend, or increased because you believed you were the best qualified. As Dolly is talking through her feelings and disappointment, Edward reminds her that Myron is their friend and even if she cannot approach him as a friend, she has to approach him as her boss to clear the air and get to a place of peace — or look for work elsewhere.

Edward also tells Dolly he was initially disappointed about not getting the promotion. The feeling didn’t last long because Greta, as soon as her promotion took effect, reached out to him and his colleagues to address concerns and discuss mutual expectations. He wasn’t the only internal candidate who applied for the general counsel job, but he was and remains the closest to Greta. They have had to navigate their friendship differently, but are constantly working on it just as they do all their other relationships.

Dolly feels like Myron just showed up on Monday morning after his promotion was announced as a different person and that he let his new title go to his head. “He doesn’t trust me to do my job,” she said, adding, “he treats everyone else better than me, it’s like he’s trying to prove that we are not friends.” Edward reminded Dolly she needed to share with Myron what she’s sharing with him, or things would not change.

Manage the human factors for long-term success

This allegory is not intended to say there is only one right way to run an in-house legal department or to promote internal staff. The intention is to point out some of the challenges in the process of promoting someone from amongst the ranks. By acknowledging that there may be hard feelings, adjustments to standing relationships, trust and other issues — and dealing with those issues with open communication, training, and coaching — the outcomes don’t have to be awkward or debilitating.

Work and personal relationships while necessarily changed can be improved, as can the productivity and efficiency of department processes and business client results. The bottom line is that challenges will exist whether peers become bosses or someone from the outside is brought in, therefore investments in managing the human factors of the transitions are key to long-term success.