Most off-site sessions took place at a nearby hotel, which Rich and his team preferred for a few reasons: it was a short drive from San Francisco, it had a nice conference center, and perhaps most important, the hotel chain was a client of Telegraph and gave the firm a special rate. While they weren’t afraid to spend money when necessary, Rich and his staff were proud of their culture of eliminating superfluous expenses.

The annual planning session was a different animal. For one, it was a two-day affair. Second, it was held at a resort called Meadowood, an understated but elegant facility in the Napa Valley, an hour’s drive north of San Francisco.

For the past three weeks since his performance review with Rich, Jamie had been observing his boss and his peers more closely than ever before. As a result, two things became clearer to him. One, Telegraph had something special going. Two, Jamie was falling further and further away from being part of it. He would have to do something drastic, and soon.

As he rode in the shuttle bus through the wine country on the way to Meadowood, Jamie felt ill, and not because of the winding roads. He hadn’t felt such pressure in his career since, well, maybe never.

By 11:00 A.M., everyone had arrived in the conference room and settled around the U-shaped table. Rich stood and delivered what, for him, was a customary opening talk. “I’ll keep this short, because we have a lot to cover during the next two days. This meeting marks our eighth consecutive year of revenue growth, profitability, and general success at Telegraph. As always, I thank you for your effort, your passion, and your commitment. I think you know that those are not empty words.” Tom could not help but crack a smile at the understated nature of his boss. Rich continued. “But let me say, as I’ve said before, that it is critical that we not take our success for granted. Some of the best companies in the world, with greater market share and brand equity than ours, have grown complacent and assumed that their continued success was inevitable, only to watch helplessly as it all slipped away.” They had heard this message before, but Rich’s sincerity never let them ignore it.

He brought the point home: “If you think about the achievements we’ve made over the years, you can trace their roots back to one place and one time: this annual session. So let’s work hard, engage one another, and find a way to suck every bit of productivity out of the next two days. And if we can, let’s have a little fun too.” Rich smiled and sat down.

Jamie was dumbfounded. Though he would not be able to admit it until months later, for the first time in his brief stint at Telegraph, he was beginning to understand why everyone seemed to admire Rich. But Jamie wouldn’t let himself go there. That would mean increasing the pain that he would ultimately feel if he failed, which was seeming more and more likely.

Rich looked over to Jamie, who was scheduled to kick off the first part of the program. “You’re up first, Jamie.”

Always able to portray calm and composure in the face of stress, Jamie began. “Okay, I’m going to make a change in the agenda. Instead of doing our team-building exercise at the beginning of the session, I’m going to move it to the end. I think that will work best. So that means we’ll begin with Tom’s overview of the strategic plan.”

No one had the slightest idea that Jamie had just panicked. To them it had seemed like a simple change, so they opened their binders and dove in.

Tom led the first discussion, which focused primarily on two potential acquisition candidates: a retail-oriented consulting firm in Sausalito and a small electronic commerce outfit in Walnut Creek. There was anything but consensus in the room about the wisdom of making either deal. For ninety minutes, the seven executives debated the merits of each transaction.

Some were in favor of both, some were against both, and still others advocated only one of the deals. Jamie needed a score-card to understand exactly who was on which side of the issue.

At one point, Tom and Rita disagreed completely about the financial feasibility of the Sausalito acquisition. Jamie was shocked by the nature of their conversation.

Tom started the exchange. “Rita, with all due respect, the legal issues you’re raising aren’t enough for us to back off from this deal. If we tried to avoid every potential legal problem, we probably wouldn’t get out of bed in the morning.”

Rita responded carefully. “Come on, Tom, you know I’m interested in the overall financial well-being of this firm as much as you are, and that I try to balance my legal responsibilities with my general management background . . .”

As usual, Tom interrupted her. “I know, Rita. You’re not a typical weenie lawyer.” For just a brief second, the room was tense. Until Rita laughed.

Sarcastically she responded, “Thanks, Tom. I appreciate that.”

Tom was relieved by her reaction, but slightly embarrassed too. “You know what I mean. It’s just that if we don’t start pulling the trigger on these types of transactions, we’re going to have a hard time fixing our overreliance on high-tech clients. We need a sense of urgency here.”

Mark, the VP of consulting, weighed in. “The thing is, Tom, I’m not sure I can absorb responsibility for another subject matter team, and I don’t know if they have the management talent to keep up with us.” He paused. “Hell, I think it might be too much for you too, especially given the growth we’re expecting in the first two quarters. I think you’d be overwhelmed.”

Tom waited for Mark to finish the sentence this time. “Come on, Mark. You’ve got to have more faith in me than that.” To Jamie’s surprise, Tom didn’t seem angry at all.

Janet, the head of marketing, added her two cents. “I agree with Mark. Tom, you’re too stretched right now, and sometimes I worry that you’re going to break.” She let them take in the comment and then continued in a different direction. “However, we decided two years ago that our new strategy included retail and electronic commerce. And we’re a little behind Greenwich in both areas. So I think that we have to find a way to get this done, even if that means Tom has to relinquish some of his responsibilities to someone else.”

This time Jamie was sure that Tom would react. And he did.

“Please, please, please, someone take away some of my responsibilities,” Tom joked. Everyone smiled at their raw COO. “In all seriousness though, I’m open to suggestions.”

Barry, Telegraph’s CFO, spoke for the first time that morning. “This is going to be harder for you than you think, Tom. Remember what happened with me last year.” Heads around the table nodded.

Rich sat and listened, as he often did, clearly following the conversation but feeling no particular need to jump in just yet.

For another ten minutes the passion and intensity in the room climbed as everyone weighed in on one side or the other. Everyone, that is, but Jamie, who felt like a spectator at a tennis match who didn’t know which side to root for.

Finally, Rita stood and brought the conversation to an abrupt halt. “Frankly, this is all just a bunch of speculation, and nobody really knows the right answer. But there is one thing I am absolutely certain about, and no one here can convince me otherwise.” That was a more definitive statement than anyone expected from the judicious legal counsel. The room was silent. “I have to go to the bathroom. Can we take a break?”

The tension evaporated with relief. Tom suggested, “Let’s take ten minutes and regroup at 12:30. I think they’re going to bring lunch in for us.” The executives broke for the phones and the rest rooms.

Everyone in the room seemed to be engaged and invigorated by the nature of the discussion so far, with the exception of Jamie. Although he maintained a confident exterior, inside he felt lost among these people. In his entire career, he had never been comfortable engaging in the kind of dialogue that he had just seen. Unconsciously he felt the need to find a chink in their armor. Anything for relief.

Rita returned to the room before the others. She was about to turn on her cell phone when Jamie approached her. “I hope you weren’t offended by Tom’s comments.”

Rita seemed a little surprised. “I wasn’t offended at all. That’s just Tom.” She paused. “You really thought they were harsh?”

Jamie mistakenly thought Rita was second-guessing herself. In fact, what she was doing was questioning Jamie’s judgment. “Yes, I did. I’m sure he meant well, but that kind of comment can cause problems if we’re not careful.”

Rita thought hard about what Jamie said. “I appreciate your concern, but I don’t think it’s a problem. If I did, I’d tell him in a New York minute.”

Jamie tried to back-pedal. “Good. Because that’s important. As long as you can confront him if he steps over the line, then that, well, that’s important.” Even Jamie thought his reply sounded inane.

At that point the others returned to the room, and Rich reconvened the meeting with his first words in almost an hour. “Okay, everyone. We’ve analyzed this every way possible. Over the past two weeks we’ve reviewed the financials, the projections, and all the potential deal breakers. I don’t think we’re lacking any critical information here. It comes down to making a decision and sticking with it. Besides, the way we execute is ultimately going to determine how successful this is anyway.”

Everyone nodded, but Jamie’s head was bouncing up and down like a jack-in-the-box. He was desperate to find a way to get connected to these people.

Rich called the question. “So, let’s decide on the Sausalito deal first. Where do we stand?” He looked at Rita.

She breathed hard. “I still think it’s too risky.”

Mark shook his head to vote no. “I agree with you,” he said, looking at Rita.

Janet weighed in: “I say we’ve got to find a way.”

Tom smiled. “I’m for it, but I agree that I need some help.”

Barry winced. “This is tough, but I think I’ll feel worse if we don’t do it than if we try and fail.”

Finally, everyone else having weighed in, Jamie spoke. “I’m all for it.” It seemed a little hollow, if not gratuitous.

With the verbal votes in, Rich did what he usually did in these circumstances. He shared his opinion and made the final decision. “Okay. This is certainly not a slam-dunk. There are very real concerns about workload and integration, and you’ve done a nice job laying them out. In fact, I’ve changed my mind three times already this morning.” His staff smiled at the subtle compliment. “However, the strategic imperative here is overwhelming. Home growing our retail practice from what we’ve got will take too long. Acquisition is eventually going to be necessary, and I don’t think it’s going to get easier next quarter, or the one after that. So let’s do it.”

Jamie looked at Mark and Rita to see how they would respond. Nothing.

Then Rita spoke. “Okay. We’ve spent a lot of time talking about this, and we don’t want to take the entire planning session on it. So let’s meet in my office next Tuesday to talk about due diligence, integration, and anything else we need to do to make this successful. I’ll e-mail an agenda to everyone tonight.”

Mark responded first. “I’ve got something on Tuesday morning, so let’s try to do it in the afternoon. I really want to be at that meeting.”

Rita nodded and made a note on her calendar.

Jamie was dumbfounded. It was as though Rita and Mark had forgotten how they had voted. He decided they must be masking their real feelings. There had to be an underlying element of resentment in this team, and Jamie decided then that the only way to take the pressure off himself was to unearth it.