It's a situation the Celtic boss had hoped to be able to observe rather than have to endure as he wanted to get all of his business done early.
However, the Hoops have managed only to bring in Holmbert Fridjonsson and Stefan Johansen, and have been thwarted in strenuous attempts to bring in a proven goalscorer and cover for defence.
They have a shopping list, and, when they fail to get a first pick in the door - as happened with a foreign striker on Thursday - Lennon and his team move to the next name.
However, as the window prepares to close, the pace and pressure increase significantly as clubs and agents try to conclude deals.
Lennon's summation of the concept of the window said it all. "It's a pain in the neck. Next Friday will be bedlam.
"You try to cram everything into the four-week period. Everyone is doing the same thing, and everyone is trying to get deals done.
"Then the last couple of days get easier and easier because clubs are willing to offload players to cut the wage bill or because players want to go.
"The last few days, you get names thrown at you from all angles. I don't think it is good for managers."
Lennon would be much more comfortable had he already been successful in his pursuit of a striker, but he revealed: "We hit the buffers yesterday on one.
"That ended quite abruptly, which is disappointing because we felt he was a very, very good player.
"We'd done a lot of work on him, a lot of to-ing and fro-ing. But in the end, no dice, so we move on to the next one.
"I can't tell you who he is because he is contracted to a club. He's not British, but it's dead in the water."
Now the pace has picked up in the chase for another target.
"The top of your list are the specific targets, and when you can't get them, you work your way down," said Lennon, as he explained their shopping MO.
"It's difficult to say you have a number one and a number two, but this particular player was high up in what we wanted.
"We couldn't get the deal done, so we have had to move on from there. We've got a couple of calls into clubs, but no direct offers.
"So we are working away and hoping we can get one or two players in by next week."
Lennon had made it clear that, with Champions League qualifiers in mid-July, this window is the main one for the club this year.
But, as the clock ticks down, he now concedes: "I don't know about the top targets, but perhaps we will still have a bit of business to do in the summer.
"We're trying to get a couple of players in now to enhance us for the second half of the season and to be ready for July. If we can't get them all in, we will look again in the summer."
Several names have already been linked to the club, and even more will be added over the next few days.
Norwich's Robert Snodgrass has been up there from the start, but Lennon insisted "We've not spoken to his representative and we've not spoken to his club.
"So the stories must be coming from down there because they are not coming from here."
Leigh Griffiths is another whose name refuses to become disassociated from the Hoops, and Lennon is noticeably more coy when asked if the Wolves striker is on his list.
"I can't say that," he replied before adding, "but he is highly thought of, put it that way."
Shopping within Scotland has not been ruled out, but Lennon made it clear the wait to see if Georgios Samaras and Joe Ledley are going to be removed from the wage bill does not have a bearing on the recruitment of anyone else.
However, the manager did admit: "It may have a bearing on the second half of the season once we get through the January window and they are still here but not tied up on deals.
"I may have to think about the team planning for next year. I have to already be thinking about the Champions League qualifiers."
The message is there for both players that, if they don't re-sign, they risk being sidelined, and Lennon said: "It's not a question of not being able to rely on them because I've always been able to do that.
"But I've got to think 'Well, they're not going to be here next season'. If that's the scenario, I may have to plan again or look at the team for next season."
With Greece in the World Cup in the summer, Samaras would suffer most if such a situation came to pass, but Lennon insisted: "That's a conundrum he faces at the minute.
"It's probably his most important contract. He's 29, and the next three or four years are the ones that will probably set him up.
"So he's giving it a lot of thought. He's an intelligent boy and has been very fair the whole way through this.
"I'm not saying we are giving up on him.
"There's still a resolution where he could be here for the next two or three years."