Claridge is a pundit for The Football League Show and Football Focus

Middlesbrough manager Gordon Strachan had a particularly busy time in the January transfer window, bringing in seven new faces - including five from his old club Celtic.

This week I look into Strachan's dealings and consider whether they will boost Boro's hopes of reaching the Championship play-offs.

I also examine Wycombe's survival prospects at the bottom of League One and offer my views on why Swindon are conceding so many late goals as they challenge for promotion at the other end of that division.

I also assess Southampton striker Rickie Lambert's chances of playing at a higher level and look at Barnet's want-away forward John O'Flynn.

If you have a question for me, you can submit it through Twitter at http://twitter.com/AskClaridge or use the form on the top right of the page.

What do you make of Gordon Strachan's January transfer signings for Middlesbrough? And will they get us into the Championship play-offs?
Kayleigh, UK

What I can't believe is the complete and utter wholesale changes that have gone on at that club when you consider Strachan didn't take over a struggling side when he got the job at the end of October - Boro were a point off the top of the table.

It's as if he went in there and immediately thought they must be in a false position because, ever since, there have been a huge number of players coming in and out of that club, even loans.

BORO'S JANUARY SIGNINGS Lee Miller (Aberdeen) Scott McDonald (Celtic) Chris Killen (Celtic) Willo Flood (Celtic) Barry Robson (Celtic) Stephen McManus (Celtic, loan) Kyle Naughton (Tottenham, loan)

Some of their fans might be thinking that Strachan shouldn't have changed so much but he is the manager now and things have got to be done his way. Sometimes you can keep things ticking over but he obviously took the view there was something wrong and has changed it.

Strachan has signed a lot of players he knows but managers always do that because they like to know what they are getting. That is half the battle - sometimes you sign someone and you don't know their character.

If you don't know their character, you could end up signing someone and two weeks later realise you've made a mistake. I've done it - signed someone and known almost instantly he is the sort of player I want but not the character I want.

A lot of Strachan's signings have come from Scotland, and it is going to take them a bit of time to adjust. The sheer number of players that have come in and out means it will take a bit of time for that team to bed down anyway.

McDonald scored 51 goals in 88 SPL games for Celtic

Before they can start thinking about winning promotion they need to sort out the problems they have had scoring goals and Strachan will be hoping that Scott McDonald can do that, after the amount he got for him at Celtic.

Adam Johnson has gone the other way, joining Manchester City, but selling him covers the cost of bringing in the new faces and it made sense because he is out of contract at the end of the season anyway.

Johnson was their best player but seeing him leave could work in Boro's favour.

We saw it at Swindon in the summer, for example, when they lost Simon Cox but brought in a few new men and became a better team.

But, after all that transfer activity, now is the time when you want to see Boro start to find some direction - you want to know where they are going under Strachan now he has put his own personality on the club by getting his own players in.

We will find out exactly which way he is going to try and go about getting them back into the Premier League but, no, I can't see them getting in the play-offs at this stage. They are not quite there just yet.

After a terrific win against Bristol Rovers away last week, and a very disappointing result against Yeovil at home on Saturday, losing 4-1, do you think Wycombe can stay up in League One?
Tyler Strange, UK

Wycombe are in a bit of trouble but they can get themselves out of it. I spoke to Leyton Orient manager Geraint Williams recently, and they have been on a great run in the last couple of weeks to charge up the table.

He said the only difference between that sort of form and them struggling is that two or three of his players are fit again.

Wycombe 1-4 Yeovil

That is what it can come down to at that level, and it is not too late for Wycombe, especially with how their manager Gary Waddock has added to his squad in the last couple of weeks with players like Gareth Ainsworth.

A run of a few wins and draws like Orient are on, which are results that Wycombe have shown they are capable of with wins like that one at Rovers, and they are out of the relegation zone.

As a promoted side, a club of Wycombe's size were always going to feel the difference when they stepped up from League Two but I think it is down to a lack of investment that they are down near the bottom of the table in the first place.

I think that is the problem that their former manager Peter Taylor saw coming but it would be lovely to see the club's budget and then make that call.

Although performing above expectations and currently occupying a play-off position, Swindon have an alarming record of letting in goals very late in the game. Of the 33 goals Town have conceded this season, 12 have been in the final five minutes of the game - leading to a loss of 14 points as a result. If matches lasted 85 minutes then Swindon would be joint-top of League One with Norwich, with three games in hand! In your experience, what are the reasons for teams letting in this number of goals late in the game and is there anything that manager Danny Wilson and Swindon's coaching staff can do to curb this wasteful habit?
Alex Higgins, England

We spoke about this on the Football League show on Saturday but I'll go into more depth here.

Swindon concede an injury-time equaliser against Charlton

If a team continually concedes late goals, it tends to mean that you lack a leader on the pitch - someone who is actually going to say 'hold on a minute, we are winning this game with five minutes to go so don't go running up the field, past the ball or try to go past people'.

You want someone who will organise that and get the other players to be tough to beat and make sure you see the game out.

You make sure people don't lose their discipline, that they stay in their positions and they are tough to break down.

I've not really played for teams which have conceded lots of late goals because I was one of the people that organised things on the pitch to prevent them. When you can see which way a game is going you have to react to it and you can't always leave it to the manager.

Swindon were winning on Saturday when Charlton equalised but it has also happened in games where they are level and going for the win but then conceded themselves.

That's the way they play - some teams will always have the emphasis on attacking, while others will be the other way round, it's getting the balance that you need and that's the art of winning games.

But sometimes it is very difficult to change your style of play, especially if it has been bringing you success.

If they had adopted a defensive or cautious stance, then they might not have won so many games to be where they are near the top of League One, so conceding is just one of those things they have to live with - but they probably get a bit nervous about it late in games now because it keeps happening.

Is there any reason why nobody from the Premier League, or even the Championship for that matter, has been linked with Rickie Lambert at Southampton? I played against him a good few years back and he's scoring almost as many in League One as he did then against amateurs but everybody is talking about Leeds striker Jermaine Beckford, when Lambert scored the same as Beckford last season when he was playing for Bristol Rovers and is currently scoring more than him now, for two distinctly weaker teams than Leeds.
Carl Arnold, Liverpool

It's probably down to Lambert's age. He turns 28 next week and he has never played outside the bottom two divisions.

He guarantees you goals in League One level. But, before you would consider him for the Premier League, he has to go up again and score in the Championship too.

Lambert has scored 23 goals for Southampton this season

Everybody has to, unless you're a kid with raw potential. I was in a similar position and I had to do it.

You do feel that, if he was going to move up, he would have gone by now but Southampton are benefiting because he is clearly a very, very good goalscorer at that level and he is also benefiting from playing in a good side that are giving him plenty of chances.

They paid going on £1m for him and not every Premier League club can afford to pay that now so he will be earning good wages and he is at a very good club - good luck to him too, because he has worked very hard to get where he is.

Beckford is the player with the greater potential to play at a higher level. But if you are saying to me 'who would you hang your hat on to score 20 goals in League One every year?' I would say Lambert.

As a Barnet fan, I don't know what to think about John O'Flynn's refusal to move to Shrewsbury. On the one hand, he obviously has a right to choose where he plays. On the other hand, we have given him his chance and now we will get nothing for him when his deal runs out this summer. How can the different interests of club and player be balanced?
George, UK

O'Flynn has obviously got something else lined up hasn't he? I would imagine he probably knows where he is going in the summer, let's put it that way. I believe he agreed terms with Shrewsbury in the January transfer window but then decided he doesn't want to sign for another League Two club.

Watch O'Flynn score twice for Barnet against Aldershot on Saturday

I can understand why too - it's well worth his while him waiting because he doesn't know whether Shrewsbury are going to get promoted.

If they want him now, there is no reason why they won't want him in the summer. He's come to Football League quite late, joining Barnet from Cork City, and he wants to better himself by trying to get a club in a higher division.

I've seen him play - he's a lively striker and I like him.

I do understand where George is coming from in that Barnet lose out when he leaves for nothing but unfortunately that is the system.

Barnet's problem is that they are no longer in the promotion picture. If this had happened three months ago, O'Flynn's decision would have made sense all round because they would have kept him for their promotion push.

But they went almost three months without winning until they beat Aldershot on Saturday and him staying is no benefit to them now - that is the way the Bosman ruling sometimes works for clubs; sometimes they benefit and other times they suffer.

So, although they miss out on a fee for O'Flynn, they have picked up players for peanuts like Albert Adomah from Harrow and non-league clubs could easily complain that system isn't fair either.

Incidentally, I'd like to know what George thinks has gone wrong at Barnet - I've no idea what has happened there in the last few weeks. They have gone from being extremely good to appalling - as if everybody has run into a brick wall.

Steve Claridge is a BBC Football League pundit who played more than 800 matches for 15 clubs over the course of a 24-year playing career. He was talking to Chris Bevan.

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